6-Aminohexanoic Acid → 6-Benzamidohexanoic acid

Participants

Reaction Steps

(Method J10) To the solution of 6-aminocaproic acid (2h) (0.982 g, 7.5 mmol) in water/dioxane (1:1) mixture (30 ml) NaOH (0.8 g, 20 mmol) in H2O (2 ml) and benzoyl chloride (1/67) (1.16 ml, 10 mmol) were added. The mixture was stirred for 6 h at room temperature and diluted with brine (150 ml). The mixture was washed with diethyl ether (2×25 ml), acidified with conc. HCl to pH 4, and extracted with ethyl acetate (4×25 ml). The organic solution was washed with brine (3×25 ml), dried (Na2SO4) and evaporated. The crude title compound (1.589 g, 90%) was purified by column chromatography on silica gel with chloroform-ethyl acetate (1:2) as eluent. 1H NMR (CDCl3, HMDS) δ: 1.18-1.85 (m, 6H); 2.34 (t, J=7.0 Hz, 2H); 3.45 (q, J=6.0 Hz, 2H); 6.27 (bs, 1H); 7.29-7.52 (m, 3H); 7.61-7.85 (m, 2H); 10.41 (bs, 1H).

Provenance & Evidence