IE37859B1 - Alkanols and their carbamate derivatives and process for preparing the same - Google Patents
Alkanols and their carbamate derivatives and process for preparing the sameInfo
- Publication number
- IE37859B1 IE37859B1 IE1084/73A IE108473A IE37859B1 IE 37859 B1 IE37859 B1 IE 37859B1 IE 1084/73 A IE1084/73 A IE 1084/73A IE 108473 A IE108473 A IE 108473A IE 37859 B1 IE37859 B1 IE 37859B1
- Authority
- IE
- Ireland
- Prior art keywords
- propyl
- hydrogen
- alkyl
- june
- reacting
- Prior art date
Links
- 150000004657 carbamic acid derivatives Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000002576 ketones Chemical class 0.000 abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000012442 inert solvent Substances 0.000 abstract 2
- PITHYUDHKJKJNQ-UHFFFAOYSA-N 2-propylpentanoyl chloride Chemical compound CCCC(C(Cl)=O)CCC PITHYUDHKJKJNQ-UHFFFAOYSA-N 0.000 abstract 1
- JXZORDPWPPTAMR-UHFFFAOYSA-N 3-propylhexan-2-ol Chemical class CCCC(C(C)O)CCC JXZORDPWPPTAMR-UHFFFAOYSA-N 0.000 abstract 1
- YKYOUMDCQGMQQO-UHFFFAOYSA-L Cadmium chloride Inorganic materials Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- -1 alkyl cadmium chloride Chemical compound 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 230000001430 anti-depressive effect Effects 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 230000001624 sedative effect Effects 0.000 abstract 1
- 239000012279 sodium borohydride Substances 0.000 abstract 1
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 1
- 230000002936 tranquilizing effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/16—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
- C07C29/145—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones with hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/125—Monohydroxylic acyclic alcohols containing five to twenty-two carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1384442 1 - Alkyl - 2 - propyl - pentanols and their carbamates LABAZ 19 June 1973 [29 June 1972] 30600/72 Heading C2C Novel compounds I (C 3 H 7 ) 2 CH-CH(OR 1 )-R in which R is C 1-4 alkyl and R 1 is hydrogen or -CONH 2 with the proviso that when R 1 is hydrogen R is other than methyl are prepared by reacting a ketone (II) (C 3 H 7 ) 2 CH-CO-R with a reducing agent (preferably sodium borohydride or hydrogen in the presence of a catalyst) in an inert solvent to form the alcohol of Formula I which if desired is reacted with phosgene at room temperature in an inert solvent followed by condensation with ammonia. Ketones II are prepared by reacting 2-npropyl-valeronitrile with the appropriate alkyl magnesium halide and hydrolysing the complex formed or by treating 2-n-propyl-valeryl chloride with the appropriate alkyl cadmium chloride. Compounds I and 3-propyl-2-hexanols have anti-depressant, tranquilizing and sedating properties and form with a carrier or excipient a pharmaceutical composition which may be administered orally, parenterally or rectally.
[GB1384442A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3060072A GB1384442A (en) | 1972-06-29 | 1972-06-29 | Pentanols and their carbamate derivatives and process for preparing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE37859L IE37859L (en) | 1973-12-29 |
| IE37859B1 true IE37859B1 (en) | 1977-10-26 |
Family
ID=10310180
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1084/73A IE37859B1 (en) | 1972-06-29 | 1973-06-28 | Alkanols and their carbamate derivatives and process for preparing the same |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS4949907A (en) |
| AR (2) | AR201005A1 (en) |
| AT (1) | AT325015B (en) |
| AU (1) | AU474132B2 (en) |
| BE (1) | BE801323A (en) |
| CA (1) | CA996946A (en) |
| CH (1) | CH576952A5 (en) |
| DE (1) | DE2332602A1 (en) |
| ES (1) | ES416424A1 (en) |
| FR (1) | FR2190445B1 (en) |
| GB (1) | GB1384442A (en) |
| HU (1) | HU168411B (en) |
| IE (1) | IE37859B1 (en) |
| NL (1) | NL7309079A (en) |
| NO (1) | NO137496C (en) |
| OA (1) | OA04535A (en) |
| SE (1) | SE387626B (en) |
| SU (2) | SU556720A3 (en) |
| ZA (1) | ZA734074B (en) |
-
1972
- 1972-06-29 GB GB3060072A patent/GB1384442A/en not_active Expired
-
1973
- 1973-06-15 ZA ZA734074A patent/ZA734074B/en unknown
- 1973-06-19 FR FR7322179A patent/FR2190445B1/fr not_active Expired
- 1973-06-21 CH CH906073A patent/CH576952A5/xx not_active IP Right Cessation
- 1973-06-21 AU AU57183/73A patent/AU474132B2/en not_active Expired
- 1973-06-22 BE BE132618A patent/BE801323A/en unknown
- 1973-06-25 AR AR248720A patent/AR201005A1/en active
- 1973-06-25 OA OA54952A patent/OA04535A/en unknown
- 1973-06-27 SU SU1930699A patent/SU556720A3/en active
- 1973-06-27 AT AT565573A patent/AT325015B/en not_active IP Right Cessation
- 1973-06-27 HU HULA828A patent/HU168411B/hu unknown
- 1973-06-27 DE DE2332602A patent/DE2332602A1/en active Pending
- 1973-06-28 IE IE1084/73A patent/IE37859B1/en unknown
- 1973-06-28 ES ES416424A patent/ES416424A1/en not_active Expired
- 1973-06-28 SE SE7309129*A patent/SE387626B/en unknown
- 1973-06-28 NO NO2691/73A patent/NO137496C/en unknown
- 1973-06-28 CA CA175,184A patent/CA996946A/en not_active Expired
- 1973-06-29 NL NL7309079A patent/NL7309079A/xx not_active Application Discontinuation
- 1973-06-29 JP JP48074322A patent/JPS4949907A/ja active Pending
- 1973-10-26 AR AR250720A patent/AR198331A1/en active
-
1974
- 1974-12-08 SU SU742080925A patent/SU625601A3/en active
Also Published As
| Publication number | Publication date |
|---|---|
| DE2332602A1 (en) | 1974-01-17 |
| JPS4949907A (en) | 1974-05-15 |
| NL7309079A (en) | 1974-01-02 |
| CH576952A5 (en) | 1976-06-30 |
| GB1384442A (en) | 1975-02-19 |
| BE801323A (en) | 1973-12-26 |
| AU474132B2 (en) | 1976-07-15 |
| AU5718373A (en) | 1975-01-09 |
| SU625601A3 (en) | 1978-09-25 |
| ES416424A1 (en) | 1976-03-01 |
| NO137496C (en) | 1978-03-08 |
| AT325015B (en) | 1975-09-25 |
| SE387626B (en) | 1976-09-13 |
| FR2190445B1 (en) | 1977-09-09 |
| AR201005A1 (en) | 1975-02-06 |
| OA04535A (en) | 1980-03-30 |
| SU556720A3 (en) | 1977-04-30 |
| CA996946A (en) | 1976-09-14 |
| FR2190445A1 (en) | 1974-02-01 |
| NO137496B (en) | 1977-11-28 |
| AR198331A1 (en) | 1974-06-14 |
| ZA734074B (en) | 1974-07-31 |
| IE37859L (en) | 1973-12-29 |
| HU168411B (en) | 1976-04-28 |
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