1,2-Dichloroethane → 8-Bromo-3-(n-propylamino)chroman

Participants

Reaction Steps

To a mixture of 8-bromo-3-aminochroman (200 mg; 0.9 mmol) in CH2Cl2 (25 ml) and 10% aqueous Na2CO3 (25 ml) was added propionyl chloride (400 mg; 2.2 mmol) and the mixture was stirred for 2 hours. The phases were separated and the organic layer was dried (MgSO4). The solvent was evaporated and the crude amide was reduced with tetrabutylammonium borohydride (400 mg, 1.6 mmol) in a boiling (1:1)-mixture (50 ml) of dichloromethane and 1,2-dichloroethane overnight. The solution was extracted with water, dried (Na2SO4) and the solvent was evaporated yielding 140 mg (58%) of 8-bromo-3-(n-propylamino)chroman.

Provenance & Evidence