2-[4-(aminomethyl)phenyl]-N-propan-2-ylacetamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Use a method similar to the General Procedure 1-2 to couple 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (162 mg, 0.38 mmol) and 4-(iso-propylcarbamoyl-methyl)-benzylamine (157 mg, 0.76 mmol). Purify by chromatography on silica gel eluting with hexane/EtOAc (9:1, 4:1, 2:1 and 1:1) to obtain 7-chloro-6-[4-(iso-propylcarbamoyl-methyl)-benzylamino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as an oil (117 mg, 64%). Purify by chromatography on silica gel eluting with hexane/EtOAc (9:1, 4:1, 2:1 and 1:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dissolve N-(tert-butoxycarbonyl)-4-(iso-propylcarbamoyl-methyl)-benzylamine (426 mg, 1.4 mmol) in DCM (5 mL). Add 4M hydrogen chloride in dioxane (3.5 mL, 14 mmol) and stir at room temperature for 1 h. Concentrate in vacuo and elute the compound through a SCX column to obtain the title compound as a white solid (281 mg, 98%). MS (ES+) m/z: 207 (M+H)+. Concentrate in vacuo elute the compound through a SCX column