C([N:8]1[CH2:30][CH2:29][C:12]2=[C:13]([CH2:20][CH2:21][O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[N:11]2[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+].CO>[Pd].ClCCl>[O:22]([CH2:21][CH2:20][C:13]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=2[N:11]2[CH2:10][CH2:9][NH:8][CH2:30][CH2:29][C:12]=12)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1(Chart D, Step 4): A dry round bottom flask is charged with 3-benzyl-11-(2-phenoxyethyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole (317 mg, 0.80 mmol), ammonium formate (254 mg, 4.0 mmol), methanol (18 mL) and dichloromethane (3.2 mL). After the addition of 10% Pd/C (64 mg) the reaction is stirred at ambient temperature for two days. The reaction mixture is filtered through a pad of celite, and the catalyst is rinsed with methanol. The filtrates are combined and concentrated to 380 mg of a crude solid. This material is recrystallized from ethyl acetate/methanol/ethyl ether to afford 239 mg of 11-(2-phenoxyethyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole as a white solid. IR (drift) 3026, 3015, 2998, 2983, 2948, 2910, 2869, 2806, 2781, 2752, 1468, 1451, 1245, 755, 746 cm−1.
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