GB731391A - Process for the production of new hydroxy-diamines - Google Patents
Process for the production of new hydroxy-diaminesInfo
- Publication number
- GB731391A GB731391A GB1844/53A GB184453A GB731391A GB 731391 A GB731391 A GB 731391A GB 1844/53 A GB1844/53 A GB 1844/53A GB 184453 A GB184453 A GB 184453A GB 731391 A GB731391 A GB 731391A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- hydroxypropyl
- methoxy
- ethyl
- radical
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title abstract 2
- -1 ethyl- Chemical group 0.000 abstract 10
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical group CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 abstract 2
- QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical group CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical compound C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 abstract 1
- ZSMRRZONCYIFNB-UHFFFAOYSA-N 6,11-dihydro-5h-benzo[b][1]benzazepine Chemical group C1CC2=CC=CC=C2NC2=CC=CC=C12 ZSMRRZONCYIFNB-UHFFFAOYSA-N 0.000 abstract 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- DJEQZVQFEPKLOY-UHFFFAOYSA-N N,N-dimethylbutylamine Chemical group CCCCN(C)C DJEQZVQFEPKLOY-UHFFFAOYSA-N 0.000 abstract 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001339 alkali metal compounds Chemical class 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000005266 diarylamine group Chemical group 0.000 abstract 1
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical group CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 abstract 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical group CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 150000003840 hydrochlorides Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 150000002642 lithium compounds Chemical class 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- ORSUTASIQKBEFU-UHFFFAOYSA-N n,n-diethylbutan-1-amine Chemical group CCCCN(CC)CC ORSUTASIQKBEFU-UHFFFAOYSA-N 0.000 abstract 1
- SNAUETXKUXDMFB-UHFFFAOYSA-N n-prop-2-enylbutan-1-amine Chemical group CCCCNCC=C SNAUETXKUXDMFB-UHFFFAOYSA-N 0.000 abstract 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical group C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
The invention comprises hydroxydiamines of the general formula <FORM:0731391/IV (b)/1> wherein Am represents an alkylamino or di-alkylamino radical in which each alkyl radical contains not more than 4 carbon atoms, the pyrrolidino or piperidino radical, R1 represents hydrogen or a methyl, ethyl, methoxy or ethoxy radical, and R2 represents a methyl, ethyl, methoxy or ethoxy radical, or R1 and R2 together represent an ethylene radical, and the preparation thereof by heating an amine of the formula Am-H with a 2, 3-epoxypropylamine of the formula <FORM:0731391/IV (b)/2> wherein R1, R2 and Am have the above significance. Amines which may be used in the above process are methyl-, ethyl-, n-propyl-, n-butyl-, allyl-, dimethyl-, methylethyl-, diethyl-, di-n-propyl-, diallyl-, di-n-butyl-, and methyl-n-butyl-amine, pyrollidine and piperidine. The hydroxydiamines may be converted into acid addition salts with inorganic and organic acids. Suitable 2,3-epoxypropylamines are the N-(2,3-epoxypropyl) derivatives of 2-methyl-, 2,21-dimethyl-, 2-ethyl-, 2-ethyl-21-methyl-, 2-methoxy-, 2,21-dimethoxy-, 2-methyl-21-methoxy-, 2-ethoxy- and 2-methyl-21-ethoxy-dipenylamine and o,o1-iminodibenzyl. In the examples the following compounds are prepared in the form of their hydrochloride salts: N-(3-pyrollidino-2-hydroxypropyl)-o,o1-ditolylamine, and the corresponding 3-diethylamino-, 3-dimethylamino- and 3-piperidino-compounds, N - (3 - methylamino - 2 - hydroxypropyl) - o - ethyldiphenylamine, N - (3-ethylamino - 2 - hydroxypropyl) - o - methoxy-diphenylamine, N - (3 - dimethylamino - 2-hydroxypropyl) - o,o1 - dimethoxydiphenylamine, N - (3 - pyrrolidino - 2 - hydroxypropyl)-o1 - ethoxydiphenylamine, N - (3 - dimethylamino - 2 - hydroxypropyl) - o,o1 - iminodibenzyl and the corresponding 3-diethylamino-, 3-pyrrolidino-, 3-piperidino-, 3-dipropylamino-, 3-ethylamino- and 3-butylamino-compounds. 2,3 - Epoxypropyldiamines of the general formula <FORM:0731391/IV (b)/3> wherein R1 and R2 have the above significance, are prepared by reacting an alkali metal compound, e.g. the sodium or lithium compound, of the required diarylamine or iminodibenzyl with epichlorhydrin. In the examples: N-(2,3 - epoxypropyl) - o,o1 - ditolylamine and N - (2,3 - epoxypropyl) - o,o1 - iminodibenzyl are prepared.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH731391X | 1952-01-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB731391A true GB731391A (en) | 1955-06-08 |
Family
ID=4532389
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1844/53A Expired GB731391A (en) | 1952-01-25 | 1953-01-22 | Process for the production of new hydroxy-diamines |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB731391A (en) |
-
1953
- 1953-01-22 GB GB1844/53A patent/GB731391A/en not_active Expired
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