Hydrochloric Acid → N-[3-(5-Bromo-2,3-dihydro-benzofuran-4-yl)-propyl]-acetamide

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH2:8][CH2:7][C:6]=2[C:10]=1[CH2:11][CH2:12][CH2:13][NH2:14].[C:15](OC(=O)C)(=[O:17])[CH3:16].Cl>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH2:8][CH2:7][C:6]=2[C:10]=1[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:17])[CH3:16]

Participants

Procedure

A solution of 3-(5-bromo-2,3-dihydro-benzofuran-4-yl)-propylamine (256 mg) in pyridine (3 ml) at 40 was treated with acetic anhydride (0.11 ml) and the solution stored overnight at 4°. The cold solution was acidified with 2N hydrochloric acid and the mixture extracted with ethyl acetate. The extracts were dried and evaporated and the residue chromatographed on silica (20 g) using dichloromethane:methanol:ammonia (100:8:1) to give the title compound as an oil which slowly solidified (175 mg).