GB653591A - Improvements in or relating to cyclic amino alcohols - Google Patents
Improvements in or relating to cyclic amino alcoholsInfo
- Publication number
- GB653591A GB653591A GB27575/48A GB2757548A GB653591A GB 653591 A GB653591 A GB 653591A GB 27575/48 A GB27575/48 A GB 27575/48A GB 2757548 A GB2757548 A GB 2757548A GB 653591 A GB653591 A GB 653591A
- Authority
- GB
- United Kingdom
- Prior art keywords
- piperidine
- methoxy
- solution
- methyl
- dihydroxy
- 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
- -1 cyclic amino alcohols Chemical class 0.000 title 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 7
- 125000003118 aryl group Chemical group 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- LTUZURZXNQLMNP-UHFFFAOYSA-N 1-ethyl-5-methoxypiperidin-3-ol Chemical compound CCN1CC(O)CC(OC)C1 LTUZURZXNQLMNP-UHFFFAOYSA-N 0.000 abstract 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 abstract 1
- YRCYKGDOLJUXGD-UHFFFAOYSA-N 5-bromo-4-methoxypent-1-ene Chemical compound COC(CBr)CC=C YRCYKGDOLJUXGD-UHFFFAOYSA-N 0.000 abstract 1
- ZWPHXSUORHWOQM-UHFFFAOYSA-N 5-methoxy-1-methylpiperidin-3-ol Chemical compound COC1CC(O)CN(C)C1 ZWPHXSUORHWOQM-UHFFFAOYSA-N 0.000 abstract 1
- NKJMJBNBMAFKDF-UHFFFAOYSA-N 5-methoxy-1-phenylpiperidin-3-ol Chemical compound C1(=CC=CC=C1)N1CC(CC(C1)OC)O NKJMJBNBMAFKDF-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 239000004593 Epoxy Substances 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000003974 aralkylamines Chemical class 0.000 abstract 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 abstract 1
- 229910001863 barium hydroxide Inorganic materials 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000012380 dealkylating agent Substances 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229940102396 methyl bromide Drugs 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- BEJBLYLRWIFFBD-UHFFFAOYSA-N n,n-dibromo-4-methylbenzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)N(Br)Br)C=C1 BEJBLYLRWIFFBD-UHFFFAOYSA-N 0.000 abstract 1
- TUDHHJQPQZFEIH-UHFFFAOYSA-N piperidine-4,4-diol Chemical compound OC1(O)CCNCC1 TUDHHJQPQZFEIH-UHFFFAOYSA-N 0.000 abstract 1
- 229940072033 potash Drugs 0.000 abstract 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 1
- 235000015320 potassium carbonate Nutrition 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
A 1-(alkyl, aryl or aralkyl)-3-hydroxy-5-alkoxy piperidine is produced by reacting together at substantially 100 DEG C. a 1 : 2-epoxy-4-alkoxy-5- halo pentane and a primary alkyl, aryl or aralkylamine. The product may be dealkylated by treatment with hydrobromic acid to form a 1-(alkyl, aryl or aralkyl)-3 : 5-dihydroxy piperidine. When the amine employed is volatile the reaction may be effected in a sealed vessel. In examples: (1) 1 : 2-epoxy-4-methoxy-5-bromo-pentane is heated in a sealed tube at 100 DEG C. with anhydrous methyl amine. After extraction with the minimum of water, the solution is saturated with potash and the separated oil extracted with benzene. On distilling the dried solution, 1 - methyl - 3 - hydroxy-5-methoxy piperidine is obtained. The latter is converted to 1-methyl-3 : 5-dihydroxy piperidine by adding it to a solution of anhydrous hydrobromic acid in glacial acetic acid and heating to 100 DEG C. until there is no more evolution of methyl bromide. The temperature is then kept at 100 DEG to 110 DEG C. for one hour and the mixture dissolved in absolute alcohol and treated with hydrated barium hydroxide. The insoluble matter is filtered off and the solution distilled to yield the dihydroxy compound; (2) as in (1) but using ethylamine instead of methylamine, the product being 1-ethyl-3-hydroxy-5-methoxy-piperidine which is converted to 1-ethyl-3 : 5-dihydroxy piperidine by treatment with hydrobromic acid; (3) 1-phenyl-3-hydroxy-5-methoxy piperidine is obtained by heating the same starting material as in (1) with aniline. The halogen atom in the 1 : 2-epoxy-4-alkoxy-5-halopentane is preferably chlorine, bromine or iodine. 1 : 2 - Epoxy - 4 - methoxy - 5 - brom - pentane is obtained by the action of a solution of perbenzoic acid in chloroform at -5 DEG C. on 1-bromo-2-methoxy-4-pentene which is itself obtained by the action of N,N-dibromo-p-toluene sulphonamide on 1 : 4-pentadiene in methyl alcohol. The Specification as open to inspection under Sect. 91 is not restricted to reaction at a specified temperature and refers to the use of any dealkylating agent in the production of the 1-(alkyl, aryl, or aralkyl)-3,5 dihydroxy piperidine. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR653591X | 1947-11-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB653591A true GB653591A (en) | 1951-05-16 |
Family
ID=9005951
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB27575/48A Expired GB653591A (en) | 1947-11-07 | 1948-10-22 | Improvements in or relating to cyclic amino alcohols |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB653591A (en) |
-
1948
- 1948-10-22 GB GB27575/48A patent/GB653591A/en not_active Expired
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