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Process for preparation of n-monosubstituted beta-amino alcohols

An alkyl and furyl technology, applied in the field of preparing N-monosubstituted β-amino alcohols and/or proton acid addition salts of the following general formula, can solve the problems of non-disclosure

Inactive Publication Date: 2013-04-24
LONZA LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Despite many attempts to discover new methods of preparation, the direct synthesis of N-monosubstituted β-ketoamines and subsequent reduction to N-monosubstituted β-aminoalcohols of the present invention has not been disclosed

Method used

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  • Process for preparation of n-monosubstituted beta-amino alcohols
  • Process for preparation of n-monosubstituted beta-amino alcohols
  • Process for preparation of n-monosubstituted beta-amino alcohols

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0095] Example 1: 3-(methylamino)-1-(thienyl-2-yl)propan-1-one hydrochloride (II,R 1 = Thiol-2-yl, R 2 = methyl)

[0096] 2-acetylthiophene (25.5g, 200mmol); Methylamine hydrochloride (14.9g, 220mmol, 1.1 equivalents); Paraformaldehyde (8.2g, 280mmol, 1.4 equivalents); HCl concentrate (1.0g); Ethanol (100mL ); 110° C., 9 hours; about 2 to 2.5 bar; ethanol (50 mL) was removed in vacuo; ethyl acetate (200 mL) was added; the yield was about 71%.

[0097] 1 H-NMR δ(DMSO-d 6 ,400MHz): 9.16(2H,s,br), 8.07(1H,dd,J=5.0,1.0), 8.01(1H,dd,J=3.8,1.0), 7.29(1H,dd,J=5.0,3.8 ), 3.49(2H,t), 3.20(2H,t), 2.56(3H,s).

[0098] 13 C-NMR δ(DMSO-d 6 ,100MHz): 189.9, 142.7, 135.4, 133.8, 128.8, 43.1, 34.6, 32.4.

Embodiment 2

[0099] Example 2: 3-(Methylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (II,R 1 = Thiol-2-yl, R 2 = methyl)

[0100] 2-Acetylthiophene (24.9 g, 197 mmol); Methylamine hydrochloride (14.8 g, 219 mmol, 1.1 equiv); Paraformaldehyde (8.3 g, 276 mmol, 1.4 equiv); HCl concentrate (1.1 g); Isopropanol (100 mL); 110° C., 8 hours; ca. 2 to 2.5 bar; addition of isopropanol (50 mL); yield ca. 65%.

Embodiment 3

[0103] Example 3: 3-(ethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (II,R 1 = Thiol-2-yl, R 2 = ethyl)

[0104] 2-acetylthiophene (6.3g, 50mmol); Ethylamine hydrochloride (6.1g, 75mmol, 1.5 equivalents); Paraformaldehyde (2.1g, 75mmol, 1.5 equivalents); HCl concentrate (0.3g); Ethanol (35mL ); 110° C., 9 hours; about 2 to 2.5 bar; ethanol (25 mL) was removed in vacuo; ethyl acetate (50 mL) was added; about 73% yield.

[0105] 1 H-NMR δ(DMSO-d 6 ,400MHz): 9.3(2H,s,br), 8.08(1H,dd), 8.00(1H,dd), 7.28(1H,dd), 3.51(2H,t), 3.20(2H,t), 2.96( 2H,q), 1.23(3H,t).

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Abstract

The invention relates to a process for the synthesis of N-monosubstituted beta-amino alcohols of formula (I) and / or an addition salt of a proton acid, wherein R<1> and R<2> independently represent alkyl, cycloalkyl, aryl or aralkyl, each being optionally further substituted with alkyl, alkoxy and / or halogen via direct preparation of N-monosubstituted beta-amino ketones of formula and its addition salts of proton acids, wherein R<1> and R<2> are as defined above.

Description

[0001] This application is a divisional application of the Chinese invention patent application No. 200910266850.5, which is a divisional application of the Chinese invention patent application No. 200610100705.6. The application date of the PCT international application on July 9, 2003 entered the Chinese national phase, and the application number was 03816223.7, and the divisional application of the invention patent application with the invention name "Preparation method of N-monosubstituted β-amino alcohol". technical field [0002] The present invention relates to the method for preparing N-monosubstituted β-aminoalcohols and / or protic acid addition salts of the general formula, [0003] [0004] The method directly synthesizes the addition salt of N-monosubstituted β-ketoamine and / or protonic acid of the following general formula. [0005] Background technique [0006] The N-monosubstituted β-aminoalcohol of general formula I is similar to (S)-(-)-3-N-methylamino-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/22C07D307/52C07D333/20C07D333/58C07C213/00C07C215/08C07C221/00C07C225/16C07D307/46
CPCC07C213/00C07C221/00C07C225/16C07D307/46C07D333/22C07D307/80C07D333/56C07D333/16C07D307/42C07D307/52C07D333/20C07C215/08C07C213/08
Inventor D·麦克尔
Owner LONZA LTD