US3963728A
Expired / Lapsed
US
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Method for preparing acylated products
Assignee: KH Neochem Co Ltd
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Filing: 1974-08-16
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Granted: 1976-06-15
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Expires: 1994-08-16
Abstract
Abstract Acylation of nitrogen containing compounds utilizing esters as acylation agents in the presence of salts of substituted pyridine compounds.
Inventors
- 👤 Yasuo Fujimoto
- 👤 Nobuhiro Nakamizo
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 10:45
CPC Classifications
C; C07; C07C; C07C273/00; C07C273/18; C07C273/1809; C07C273/1836; C07K; C07K1/00; C07K1/06; C07K1/08; C07K1/084
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
119 words
In a process for preparing a carboxylic acid amide which comprises acylating a heterocyclic amine with an ester derived from an aliphatic or aromatic carboxylic acid, the improvement which comprises carrying out said acylation in the presence of an alkali-metal salt, an alkaline earth metal salt or a quaternary ammonium salt of a pyridine compound whose pyridine nucleus is directly substituted by a hydroxy group or a mercapto group, and optionally by at least one member selected from the group consisting of an alkyl group having from 1 to 6 carbon atoms, an aryl group, an aralkyl group, an alkoxy group having from 1 to 6 carbon atoms, a nitro group, a cyano group and a fused benzene ring.
Claim 2
Dependent Claim
119 words
In a process for preparing a carboxylic acid amide which comprises acylating a heterocyclic amine with an ester derived from an aliphatic or aromatic carboxylic acid, the improvement which comprises carrying out said acylation in the presence of an alkali-metal salt, an alkaline earth metal salt or a quaternary ammonium salt of a pyridine compound whose pyridine nucleus is directly substituted by a hydroxy group or a mercapto group, and optionally by at least one member selected from the group consisting of an alkyl group having from 1 to 6 carbon atoms, an aryl group, an aralkyl group, an alkoxy group having from 1 to 6 carbon atoms, a nitro group, a cyano group and a fused benzene ring.
Claim 3
Dependent Claim
17 words
The process of claim 1 wherein the pyridine compound is a pyridine, a quinoline or an isoquinoline.
Claim 4
Dependent Claim
20 words
The process of claim 1 wherein the acylation is carried out in the presence of a salt of a hydroxypyridine.
Claim 5
Dependent Claim
11 words
The process of claim 1 wherein said heterocyclic amine is piperidine.
Claim 6
Dependent Claim
36 words
The process of claim 1 wherein said heterocyclic amine is piperidine, wherein said ester is benzyloxycarbonyl glycine phenyl ester, wherein said salt is the sodium salt of 3-hydroxypyridine and wherein said carboxylic acid amide is N-(benzyloxycarbonylglycyl)-piperidine.
Claim 7
Dependent Claim
14 words
The process of claim 3 wherein said salt is the sodium salt of 2-hydroxypyridine.
Claim 8
Dependent Claim
13 words
The process of claim 1 wherein said aryl group is phenyl or tolyl.
Claim 9
Dependent Claim
11 words
The process of claim 1 wherein said aralkyl group is benzyl.
Claim 10
Dependent Claim
18 words
The process of claim 1 wherein said quaternary ammonium salt is a lower alkyl tetra-substituted quaternary ammonium salt.
Claim 11
Dependent Claim
89 words
In a process for preparing a carboxylic acid amide which comprises acylating a heterocyclic amine whose amino nitrogen atom has at least one hydrogen atom thereon, with a carboxylic acid ester derived from an aliphatic or aromatic carboxylic acid, the improvement which comprises conducting said acylation in the presence of a catalyst composed of an alkali metal salt, an alkaline earth metal salt or a quaternary ammonium salt of a pyridine, quinoline or isoquinoline compound whose pyridine nucleus is directly substituted by a hydroxy group or a mercapto group.
Claim 12
Dependent Claim
89 words
In a process for preparing a carboxylic acid amide which comprises acylating a heterocyclic amine whose amino nitrogen atom has at least one hydrogen atom thereon, with a carboxylic acid ester derived from an aliphatic or aromatic carboxylic acid, the improvement which comprises conducting said acylation in the presence of a catalyst composed of an alkali metal salt, an alkaline earth metal salt or a quaternary ammonium salt of a pyridine, quinoline or isoquinoline compound whose pyridine nucleus is directly substituted by a hydroxy group or a mercapto group.
Claim 13
Dependent Claim
55 words
The process of claim 10 wherein said pyridine nucleus is also directly substituted by at least one member selected from the group consisting of an alkyl group of 1 to 6 carbon atoms, an aryl group, an aralkyl group, an alkoxy group of 1 to 6 carbon atoms, a nitro group and a cyano group.
References Cited (Backward Citations)
US2524422A
Cited
US3660485A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-06-15 | 1979-12-15 | 1980-06-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-06-15 | 1983-12-15 | 1984-06-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-06-15 | 1987-12-15 | 1988-06-15 | $7700.00 | Window Closed / Lapsed |