Cyclopentanecarboxylic acid, 1-[(1-oxopentyl)amino]- synthesis
- Product Name:Cyclopentanecarboxylic acid, 1-[(1-oxopentyl)amino]-
- CAS Number:15026-80-9
- Molecular formula:C11H19NO3
- Molecular Weight:213.27
Yield:15026-80-9 68%
Reaction Conditions:
Stage #1: 1-aminocyclopentanecarboxylic acid hydrochloride;n-valeryl chloridewith sodium hydroxide;tetrabutylammomium bromide in water;toluene at 0 - 5; for 2 h;
Stage #2: in water;Product distribution / selectivity;Acidic aqueous solution;
Steps:
9
EXAMPLE 9; Preparation of 1-Valeramidocyclopentanecarboxylic acid; In a 3 necked 250 ml round bottom flask equipped with mechanical stirrer, was charged with sodium hydroxide solution (24.1 g dissolved in 100 ml water) and 1-aminocyclopentane carboxylic acid hydrochloride (25 g) and chilled to 0° C. under stirring. Tetra butyl ammonium bromide (0.25 g) was added to the reaction mixture followed by slow addition of a solution of valeroyl chloride (27.5 g) in toluene (20 ml) during one hour at 0-5° C. under stirring. The reaction mass was stirred for 1 hour at 0-5° C. The reaction mixture was diluted with water (100 ml) toluene (20 ml) and stirred for 15 minutes. The two phases were separated. The aqueous phase was washed with toluene (20 ml). Aqueous phase was chilled to 10° C. and acidified with hydrochloric acid and stirred it for 1 hour. The product was filtered and washed with water. The product was dried at 60° C. till constant weight. (Yield: 22 g; 68%). 1H-NMR (DMSOd6): δ ppm 0.819 (t,3H); 1.16-128(sex,2H); 1.37-1.47(quent,2H); 1.59(m,4H); 1.79-1.84(m,2H); 1.97-2.05 (m,4H); 8.02(s, 1H); 12.0 (Broad singlet, 1H).
References:
US2007/99973,2007,A1 Location in patent:Page/Page column 14
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