Dimethylformamide → 3-(Dimethylamino)-1-propanol

Participants

Reaction Steps

The procedure used in Example 233 is followed, but starting from 500 mg of 4-(5-carboxy-1H-benzimidazol-2-yl)-9H-fluoren-9-one, obtained in stage 1 of Example 241, 261 μl of 3-dimethylaminopropanol, 280 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI), 50 mg of N,N-dimethylaminopyridine (DMAP) in a mixture of 4 ml of dichloromethane, 2 ml of tetrahydrofuran and 1 ml of dimethylformamide, for 20 hours at room temperature. After purification by flash chromatography on silica gel (40-63 μm), eluting with a mixture of dichloromethane and methanol (9/1 by volume) and then dichloromethane and ammonia as a 7N solution in methanol (9/1 by volume), in this way we obtain 582 mg of 4-{5-[(3-dimethylaminopropyl)carbonyloxy]-1H-benzimidazol-2-yl}-9H-fluoren-9-one, in the form of a yellow resin, which is used as it is in the following stage, with the following characteristics:

Provenance & Evidence