4-Amino-1-butanol → 4-(1,2-Benzisoxazol-3-ylamino)-1-butanol

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-chloro-1,2-benzisoxazole (0.08 mol), 4-amino-1-butanol (0.24 mol) and KI (1 g) was stirred for 4 days at 80° C. The reaction mixture was cooled, dissolved in CH2Cl2 and purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5). The pure fractions were collected and the solvent was evaporated, yielding 15.4 g (93%) of 4-(1,2-benzisoxazol-3-ylamino)-1-butanol (interm. 1). b) Thionyl chloride (0.048 mol) was cooled to 0° C. A solution of intermediate (1) (0.048 mol) in CHCl3 (20 ml) was added dropwise and the reaction mixture was stirred overnight at RT. The solvent was evaporated. The residue was washed with water. The reaction mixture was extracted with CH2Cl2. The separated organic layer was dried (MgSO4), filtered, and the solvent was evaporated, yielding 10.4 g of ON—(4-chloro-butyl)-1,2-benzisoxazol-3-amine (interm. 2).

Provenance & Evidence