US4473694A
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US
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Process for the preparation of polysubstituted α-aminoacetamides
Assignee: Noveon IP Holdings Corp
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Filing: 1982-09-29
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Granted: 1984-09-25
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Expires: 2002-09-29
Abstract
Abstract Process for the synthesis of hindered polysubstituted α-amino acetamides which comprises first reacting an α-haloacetamide with a base to form an intermediate α-lactam which in turn is reacted with a primary or secondary amine. The product thus obtained can comprise a multifunctional compound having one or more hindered amino moieties. These compounds are highly effective as UV stabilizers in a variety of plastics, especially the alpha monoolefins.
Inventors
- 👤 John T. Lai
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 11:24
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/04; C07D295/14; C07D295/145; C07D295/15; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/56; C07D211/58
Claims Analysis
Total Claims: 5
Claim 1
Independent Claim
265 words
A process for the preparation of polysubstituted α-aminoacetamides having the formula ##STR11## wherein R 1 and R 4 are independently selected from the group consisting of alkyl of 1 to 8 carbons; phenyl; alkyl-, alkoxy-, alkylamino-, dialkylamino- or halo-substituted phenyl having 1 to 3 said substitutents wherein alkyl groups have 1 to 12 carbons; cycloalkyl of 4 to 8 carbons; piperidinyl; 2,2,6,6-tetra(lower alkyl)piperidinyl; alkenyl of 2 to 6 carbons, or R 4 is hydrogen or R 4 is a group ##STR12## where n is 1 to 6; R 2 and R 3 are independently selected from the group consisting of hydrogen and alkyl of 1 to 6 carbons; and R 5 is hydrogen or alkyl of 1 to 6 carbons or R 1 and R 5 together with the nitrogen form a heterocyclic group selected from the group consisting of piperidinyl, morpholinyl and piperazinyl, said process comprises (a) reacting an α-haloacetamide of the formula ##STR13## wherein R 2 , R 3 and R 4 are as defined above or R 4 is ##STR14## and X is chlorine or bromine; with a stoichiometric amount of a base selected from the group consisting of sodium hydroxide and potassium hydroxide, to form an intermediate α-lactam, and thereafter (b) reacting said intermediate α-lactam with an amine of the formula ##STR15## wherein R 1 and R 5 are as defined above, said reaction being carried out in an inert atmosphere, at a temperature of from 20° C. to about 100° C. and the molar ratio of an amine to an α-haloactamide being in the range of from 1:1 to 100:1.
Claim 2
Dependent Claim
265 words
A process for the preparation of polysubstituted α-aminoacetamides having the formula ##STR11## wherein R 1 and R 4 are independently selected from the group consisting of alkyl of 1 to 8 carbons; phenyl; alkyl-, alkoxy-, alkylamino-, dialkylamino- or halo-substituted phenyl having 1 to 3 said substitutents wherein alkyl groups have 1 to 12 carbons; cycloalkyl of 4 to 8 carbons; piperidinyl; 2,2,6,6-tetra(lower alkyl)piperidinyl; alkenyl of 2 to 6 carbons, or R 4 is hydrogen or R 4 is a group ##STR12## where n is 1 to 6; R 2 and R 3 are independently selected from the group consisting of hydrogen and alkyl of 1 to 6 carbons; and R 5 is hydrogen or alkyl of 1 to 6 carbons or R 1 and R 5 together with the nitrogen form a heterocyclic group selected from the group consisting of piperidinyl, morpholinyl and piperazinyl, said process comprises (a) reacting an α-haloacetamide of the formula ##STR13## wherein R 2 , R 3 and R 4 are as defined above or R 4 is ##STR14## and X is chlorine or bromine; with a stoichiometric amount of a base selected from the group consisting of sodium hydroxide and potassium hydroxide, to form an intermediate α-lactam, and thereafter (b) reacting said intermediate α-lactam with an amine of the formula ##STR15## wherein R 1 and R 5 are as defined above, said reaction being carried out in an inert atmosphere, at a temperature of from 20° C. to about 100° C. and the molar ratio of an amine to an α-haloactamide being in the range of from 1:1 to 100:1.
Claim 3
Dependent Claim
24 words
A process of claim 1 wherein the molar ratio of an amine to an α-haloacetamide is in the range of from 1.2:1 to 20:1.
Claim 4
Dependent Claim
33 words
A process of claim 1 wherein the amine is selected from the group consisting of t-butylamine, t-octylamine, aniline, alkyl substituted aniline, isopropyl amine, propyl amine, 4-amino-2,2,6,6-tetramethyl-piperidine, allyl amine, morpholine, N-methyl-aniline, and diethyl amine.
Claim 5
Dependent Claim
24 words
A process of claim 1, wherein the α-halo-acetamide is selected from the group consisting of α-chloro-α,α-dimethyl-N-phenylacetamide, α-bromo-α,α-dimethyl-N-phenylacetamide, α-bromo-α,α-dimethyl-N-(t-butyl)acetamide, α-bromo-α,α-dimethylacetamide, N,N'[1,2-ethane-bis(α-bromo-α,α-diethyl acetamide)], and α-bromo-α,α-dimethyl-N-(2,2,6,6-tetramethyl-4-piperidinyl) acetamide.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-09-25 | 1988-03-26 | 1988-09-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-09-25 | 1992-03-26 | 1992-09-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-09-25 | 1996-03-26 | 1996-09-25 | $7700.00 | Window Closed / Lapsed |