US4148824A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Manufacture of 1-disubstituted aminoalk-2-yn-4-ols
Assignee: BASF SE
•
Filing: 1977-08-15
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Granted: 1979-04-10
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Expires: 1997-08-15
Abstract
Abstract The manufacture of N-disubstituted 1-aminoalk-2-yn-4-ols by reacting a secondary amine, e.g. a dialkylamine, formaldehyde and an acetylene-alcohol by a Mannich reaction, using a copper catalyst, takes place with better yield and at a higher rate if carried out in the presence of iodine or of a bromide or iodide.
Inventors
- 👤 Herwig Hoffmann
- 👤 Heinz Graefje
- 👤 Wolfgang Koernig
- 👤 Siegfried Winderl
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 16:55
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/04; C07D295/08; C07D295/084
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
69 words
A process for the manufacture of an N-disubstituted 1-aminoalk-2-yn-4-ol by reaction of an optionally 3-mono- or di-substituted 3-hydroxypropyne with formaldehyde and an aliphatic secondary amine in aqueous acid solution in the presence of a copper compound, in accordance with the Mannich reaction, wherein the reaction is carried out in the presence of a bromide or iodide which is soluble in the reaction mixture, or in the presence of iodine.
Claim 2
Dependent Claim
69 words
A process for the manufacture of an N-disubstituted 1-aminoalk-2-yn-4-ol by reaction of an optionally 3-mono- or di-substituted 3-hydroxypropyne with formaldehyde and an aliphatic secondary amine in aqueous acid solution in the presence of a copper compound, in accordance with the Mannich reaction, wherein the reaction is carried out in the presence of a bromide or iodide which is soluble in the reaction mixture, or in the presence of iodine.
Claim 3
Dependent Claim
134 words
A process for the manufacture of a 1-disubstituted aminoalk-2-yn-4-ol of the formula (I) ##STR2## where R 1 is hydrogen or an aliphatic hydrocarbon radical and R 2 is hydrogen or an aliphatic or aromatic hydrocarbon radical, or R 1 and R 2 together with the carbon atom to which they are attached form a cycloaliphatic hydrocarbon radical, and R 3 and R 4 are each an aliphatic hydrocarbon radical, by reacting an alkynol of the formula ##STR3## with formaldehyde and a secondary amine of the formula R 3 R 4 NH in acid solution in the presence of a copper compound, in accordance with the Mannich reaction, wherein the reaction is carried out in the presence of a bromide or iodide which is soluble in the reaction mixture, or in the presence of iodine.
Claim 4
Dependent Claim
134 words
A process for the manufacture of a 1-disubstituted aminoalk-2-yn-4-ol of the formula (I) ##STR2## where R 1 is hydrogen or an aliphatic hydrocarbon radical and R 2 is hydrogen or an aliphatic or aromatic hydrocarbon radical, or R 1 and R 2 together with the carbon atom to which they are attached form a cycloaliphatic hydrocarbon radical, and R 3 and R 4 are each an aliphatic hydrocarbon radical, by reacting an alkynol of the formula ##STR3## with formaldehyde and a secondary amine of the formula R 3 R 4 NH in acid solution in the presence of a copper compound, in accordance with the Mannich reaction, wherein the reaction is carried out in the presence of a bromide or iodide which is soluble in the reaction mixture, or in the presence of iodine.
Claim 5
Dependent Claim
19 words
A process as claimed in claim 1, carried out in the presence of an alkali metal bromide or iodide.
Claim 6
Dependent Claim
23 words
A process as claimed in claim 1, carried out at a pH of 2 to 7 in the presence of a mineral acid.
Claim 7
Dependent Claim
20 words
A process as claimed in claim 1, wherein the copper compound is a copper(II) salt soluble in the reaction mixture.
Claim 8
Dependent Claim
21 words
A process as claimed in claim 4, carried out using copper (II) chloride, nitrate, acetate or sulfate as the copper compound.
Claim 9
Dependent Claim
14 words
A process as claimed in claim 1, carried out at 85° to 95° C.
References Cited (Backward Citations)
US3448153A
Cited
US3520932A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-04-09 | 1982-10-09 | 1983-04-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-04-09 | 1986-10-09 | 1987-04-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-04-09 | 1990-10-09 | 1991-04-10 | $7700.00 | Window Closed / Lapsed |