GB783627A - Improvements in or relating to methods of preparing chemical compounds containing the pyrrocoline nucleus and new chemical compounds produced thereby - Google Patents
Improvements in or relating to methods of preparing chemical compounds containing the pyrrocoline nucleus and new chemical compounds produced therebyInfo
- Publication number
- GB783627A GB783627A GB69055A GB69055A GB783627A GB 783627 A GB783627 A GB 783627A GB 69055 A GB69055 A GB 69055A GB 69055 A GB69055 A GB 69055A GB 783627 A GB783627 A GB 783627A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bis
- pyridyl
- pyrrocoline
- dimethylaminomethyl
- pentan
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Abstract
The invention comprises pyrrocoline derivatives of the general formula <FORM:0783627/IV (a)/1> (wherein R1 and R2 may be the same or different and each represent hydrogen or an alkyl group of 1-6 carbon atoms or jointly form part of a 5, 6 or 7-membered ring fused to the pyrrocoline nucleus, and R3 and R4 represent alkyl groups), and the preparation of pyrrocoline derivatives by reacting acetic anhydride with 3-(2-pyridyl)-1 : 5 - di - tertiary - aminopentan-3-ols. Examples describe the preparation of: (1) 6-acetyl - 10 - dimethylaminomethylcyclohexa(a)-pyrrocoline from 2 : 6 - bis - (dimethylaminomethyl) - 1 - (2 - pyridyl) - cyclohexan - 1 - ol; (2) 6 - acetyl - 11 - dimethylaminomethylcyclohepta (a) pyrrocoline (isolated as its acid oxolate) from 2 : 7 - bis - (dimethylaminomethyl) - 1 - (2-pyridyl)-cycloheptan-1-ol; (3) 3-acetyl-1-(b -dimethylaminoisopropyl) - 2 - methylpyrrocoline from 2 : 4 - bis - (dimethylaminomethyl) - 3 - (2-pyridyl) - pentan - 3 - ol; (4) 1 - (b - dimethylaminoethyl) - 3 - acetylpyrrocoline (the oxalate of which is described) from 1 : 5-bis-(dimethylamino) - 3 - (2 - pyridyl) - pentan - 3 - ol; (5) 1-(b -dimethylaminoethyl) - 2 - methyl - 3 - acetylpyrrocoline or 1 - (b - dimethylaminoisopropyl-3-acetylpyrrocoline, or a mixture thereof, from 1 : 5 - bis - (dimethylamino) - 2 - methyl - 3 - (2 - pyridyl) - pentan - 3 - ol. Reference is also made to the preparation (in inferior yields) of the corresponding propionyl compounds by replacing acetic anhydride by propionic anhydride. Starting materials. 3 - (2 - Pyridyl) - 1 : 5 - di - tertiary - aminopentan - 3 - ols of the general formula <FORM:0783627/IV (a)/2> are prepared by the action of pyridyl lithium on ditertiary-amino ketones of the general formula <FORM:0783627/IV (a)/3> by a process analogous to that of Specification 689,234. 2 : 6 - Bis - (dimethylaminomethyl)-cyclohexan - 1 - one, 2 : 7 - bis - dimethylaminomethyl)-cycloheptan-1-one and 2 : 4-bis-(dimethylaminomethyl)-pentan-3-one (from which the starting materials of Examples (1) to (3) are prepared) are obtained (initially as dihydrochlorides) by the action of dimethylamine hydrochloride and aqueous formaldehyde at steam-bath temperature on cyclohexanone, cycloheptanone and diethyl ketone respectively.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB69055A GB783627A (en) | 1955-01-10 | 1955-01-10 | Improvements in or relating to methods of preparing chemical compounds containing the pyrrocoline nucleus and new chemical compounds produced thereby |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB69055A GB783627A (en) | 1955-01-10 | 1955-01-10 | Improvements in or relating to methods of preparing chemical compounds containing the pyrrocoline nucleus and new chemical compounds produced thereby |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB783627A true GB783627A (en) | 1957-09-25 |
Family
ID=9708813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB69055A Expired GB783627A (en) | 1955-01-10 | 1955-01-10 | Improvements in or relating to methods of preparing chemical compounds containing the pyrrocoline nucleus and new chemical compounds produced thereby |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB783627A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003051819A1 (en) * | 2001-12-14 | 2003-06-26 | Grünenthal GmbH | Substituted 1,5-diaminopentan-3-ol compounds |
-
1955
- 1955-01-10 GB GB69055A patent/GB783627A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003051819A1 (en) * | 2001-12-14 | 2003-06-26 | Grünenthal GmbH | Substituted 1,5-diaminopentan-3-ol compounds |
| JP2005511781A (en) * | 2001-12-14 | 2005-04-28 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | Substituted 1,5-diaminopentan-3-ol compounds |
| US7569585B2 (en) | 2001-12-14 | 2009-08-04 | Gruenenthal Gmbh | 1, 5-diaminopentan-3-ol compounds and related treatment methods |
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