Hydrochloric Acid → HCID 67017887, compound

Participants

Reaction Steps

A solution of 364 mg (1.04 mmol) of benzo[b]thiophene-2-carboxylic acid[2-(3,4-di-chloro-phenyl)-ethyl]-amide in 10 ml of THF was added dropwise to 5.2 ml of a 1 molar solution of BH3-THF complex in THF at 0° C. The reaction mixture was stirred for 30 min at RT and then heated to reflux over night. Then 2 ml of 6 N HCl were added very carefully at ambient temperature and the mixture was heated again to reflux for 2 hours. After cooling to RT, the pH was adjusted to 8-9 by addition of 1 N sodium hydroxide solution and the mixture was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried with magnesium sulfate, filtered and concentrated. Final purification of the residue (silica gel; dichloromethane/methanol 95:5) yielded 113 mg (32%) of benzo[b]thiophen-2-ylmethyl-[2-(3,4-dichloro-phenyl)-ethyl]-amine as off-white solid. MS (ISP) 336.2 (M+H)+.

Provenance & Evidence