Hydrochloric Acid → HCID 59828919, compound

Participants

Reaction Steps

Bubble hydrogen chloride into a solution of 6-{-4-[N-(tert-butoxycarbonyl)-N-(cyclohexyl)-aminomethyl]-benzylamino}-7-chloro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (355 mg, 0.6 mmol) in EtOAc (5 mL) at room temperature. Stir the mixture for 1 h, and concentrate in vacuo. Dissolve the residue in methanol (5 mL) and add water (2 mL) and K2CO3 (1 g, 7.2 mmol). Stir the mixture at room temperature overnight. Concentrate the mixture in vacuo and partition the residue between water (20 mL) and DCM (20 mL). Extract the aqueous phase with DCM (2×20 mL). Dry the combined organic extracts over Na2SO4, filter, and concentrate in vacuo. Purify by reverse phase chromatography [Phenomonex C18(2) column (5×25 cm) eluting with a gradient of water:acetonitrile (0.1% TFA in each) 9:1 through 2:3 over 50 min, 118 mL/min]. Concentrate pure fractions and apply to a SCX column (3.5 g) eluting with methanol and 3N ammonia in methanol to obtain 7-chloro-6-{4-[N-(cyclohexyl)-aminomethyl]-benzylamino}-2,3,4,5-tetrahydro-1H-benzo[d]azepine (204 mg, 86%).

Provenance & Evidence