GB765874A - 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
- GB765874A GB765874A GB3551353A GB3551353A GB765874A GB 765874 A GB765874 A GB 765874A GB 3551353 A GB3551353 A GB 3551353A GB 3551353 A GB3551353 A GB 3551353A GB 765874 A GB765874 A GB 765874A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyridyl
- acetyl
- phenyl
- chlorophenyl
- methyl
- 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)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
A method of preparing compounds containing the pyrrocoline nucleus comprises reacting a 1-(2 - pyridyl) - 3 - tertiary aminopropan - 1 - ol or a 1 - (2 - pyridyl) 3 - tertiary aminoprop - 1 - ene with acetic anhydride and separating the resulting pyrrocoline from the reaction mixture. The process is applicable to the reaction with acetic anhydride of compounds of the formula: <FORM:0765874/IV(b)/1> and <FORM:0765874/IV(b)/2> respectively, in which R1 is a phenyl or 2-thienyl group (either of which may carry as substituents chloro, bromo, alkyl or alkoxy groups), a 2-pyridyl or an alkyl group; R2 is hydrogen or a methyl or phenyl group; or R1 and R2 form a fully reduced cyclic structure having 5, 6, or 7 carbon atoms; R3 is hydrogen, or when R4 is hydrogen, is a methyl or phenyl group; R4 is hydrogen or methyl, except that when R1 is 2-pyridyl, R4 is hydrogen; NR5R6 is a tertiary amino group in which R5 and R6 may either be alkyl groups or together form a cyclic structure; R7 is phenyl or thienyl, which may carry substituents as listed for R1, the product being a pyrrocoline of the general formula: <FORM:0765874/IV(b)/3> in which R8 is an acetyl group or, when R3 is methyl or phenyl, R8 is methyl or phenyl. Reference is also made to the use of propionic anhydride. In examples: (1) 1-p-chlorophenyl - 1 - (2-pyridyl) - 3 - pyrrolidinopropan - 1 - ol is boiled with acetic anhydride to give 3-acetyl-1-p - chlorophenylpyrrocoline; (2) 1 - p - chlorophenyl - 1 - (2 - pyridyl) - 3 - pyrrolidinoprop - 1 -ene refluxed with acetic anhydride, acetic acid and sodium acetate gives the same product as in (1); (3) and (4) 3-acetyl-1-phenylpyrrocoline is prepared similarly from 1 - phenyl - 1 - (2-pyridyl) - 3 - pyrrolidinopropan - 1 - ol and 1 phenyl - 1 - (2 - pyridyl) - 3 - pyrrolidinoprop - 1-ene respectively. In further examples there are similarly prepared (from starting materials which include the carbinols described below or the corresponding allylamines) (5) and (6) 3 - acetyl - 2 - methyl - 1 - phenylpyrrocoline; (7) and (8) 3 - acetyl - 1 - p - chlorophenyl - 2-methyl - pyrrocoline; (9) and (10) 3 - acetyl-1 : 2 - diphenylpyrrocoline (11) 3 - acetyl - 1 - p - chlorophenyl - 2 - phenylpyrrocoline; (12) and (13) 1 - phenyl - 3 - methylpyrrocoline; (14) 1 - p - chlorophenyl - 3 - methylpyrrocoline; (15) and (16) 1 : 3 - diphenylpyrrocoline; (17) 3 - acetyl - 1 - p - anisylpyrrocoline; (18) 3-acetyl - 1 - o - tolylpyrrocoline; (19) 3 - acetyl-8 - methyl - 1 - phenylpyrrocoline; (20) 3-acetyl - 8 - methyl - 1 - p - chlorophenylpyrrocoline; (21) 3 - acetyl - 1 - (5 - chlorothienyl-2) pyrrocoline; (22) 3 - acetyl - 1 - (2 - pyridyl) pyrrocoline; (23) 3 - acetyl - 1 - methylpyrrocoline; (24) 3 - acetyl - 1 - ter - butylpyrrocoline; (25) 6 - acetyl - cyclohexa (9) - pyrrocoline for which the starting material, 2-dimethylaminomethyl - 1 - (2 - pyridyl) - cyclohexan - 1 - ol is prepared by the reaction of 2 - dimethylaminomethylcyclohexan - 1 - one with pyridyllithium. New carbinols, prepared for use as starting materials by the method of Specification 689,234, are 1-phenyl-1-(2-pyridyl)-3-piperidinoisobutan - 1 - ol 1 - p - chlorophenyl - 1 - (2-pyridyl) - 3 - piperidinoisobutan - 1 - ol, 1 : 2-diphenyl - 1 - (2 - pyridyl) - 3 - piperidinopropan-1 - ol, 1 - p - chlorophenyl - 2 - phenyl - 1 - (2-pyridyl) - 3 - pyrrolidinopropan - 1 - ol, 1-phenyl - 1 - (2 - pyridyl) - 3 - piperidinobutan-1 - ol, 1 - p - chlorophenyl - 1 - (2 - pyridyl) - 3 - pyrrolidinobutan - 1 - ol, 1 : 3 - diphenyl - 1 - (2-pyridyl) - 3 - piperidinopropan - 1 - ol 1 - phenyl - 1 - (3 - picolyl - 2) - 3 - pyrrolidinopropan- 1-ol, 1 - p - chlorophenyl - 1 - (3 - picolyl - 2) - 3-pyrrolidinopropan - 1 - ol, 1 - o - tolyl - 1 - (2-pyridyl) - 3 - piperidinopropan - 1 - ol, 2 - (2-pyridyl) - 4 - piperidinobutan - 2 - ol, 3 - (2-pyridyl) - 2 : 2 - dimethyl - 5 - piperidinopentan-3 - ol, and 1 : 1 - di - (2 - pyridyl) - 3 - dimethylaminopropan-1-ol. As intermediates for such carbinols are prepared 1-phenyl-3-piperidinobutan - 1 - one (by reacting piperidine with crotonophenone), 1 - p - chlorophenyl - 3 - pyrrolidinobutan - 1 - one (by reacting pyrrolidine with p - chlorocrotonophenone), 1 : 3 - diphenyl - 3 - piperidinopropan - 1 - one (by reacting benzalacetophenone with piperidine), and 1 - phenyl - 3 - piperidinoisobutan - 1 - one, 1-p - chlorophenyl - 3 - piperidinoisobutan - 1-one, 1 : 2 - diphenyl - 3 - piperidinopropan - 1-one, 1 - p - chlorophenyl - 2 - phenyl - 3 - pyrrolidinopropan - 1 - one, 4 - piperidinobutan - 1-one and 5 - piperidino - 2 : 2 - dimethylpentan-3-one (by the Mannich reaction). Specifications 701,445 and 719,276 also are referred to.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3551353A GB765874A (en) | 1953-12-21 | 1953-12-21 | 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 |
---|---|---|---|
GB3551353A GB765874A (en) | 1953-12-21 | 1953-12-21 | 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 |
---|---|
GB765874A true GB765874A (en) | 1957-01-16 |
Family
ID=10378580
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3551353A Expired GB765874A (en) | 1953-12-21 | 1953-12-21 | 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) | GB765874A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3120519A (en) * | 1959-05-08 | 1964-02-04 | Ciba Geigy Corp | Pyridyl alkenes |
DE10261091A1 (en) * | 2002-12-20 | 2004-07-01 | Grünenthal GmbH | Saturated and unsaturated heteroarylcycloalkylmethyl amines |
WO2022065938A1 (en) * | 2020-09-28 | 2022-03-31 | 아주대학교산학협력단 | Compound for aggregation-induced emission, composition for cell imaging using same, and use as cell-imaging contrast agent |
-
1953
- 1953-12-21 GB GB3551353A patent/GB765874A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3120519A (en) * | 1959-05-08 | 1964-02-04 | Ciba Geigy Corp | Pyridyl alkenes |
DE10261091A1 (en) * | 2002-12-20 | 2004-07-01 | Grünenthal GmbH | Saturated and unsaturated heteroarylcycloalkylmethyl amines |
US7384961B2 (en) | 2002-12-20 | 2008-06-10 | Gruenenthal Gmbh | Saturated and unsaturated heteroarylcycloalkylmethyl amines as anti-depressants |
WO2022065938A1 (en) * | 2020-09-28 | 2022-03-31 | 아주대학교산학협력단 | Compound for aggregation-induced emission, composition for cell imaging using same, and use as cell-imaging contrast agent |
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