[C:1]([NH:5][CH:6]1[CH2:10][C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:7]1)([CH3:4])([CH3:3])[CH3:2].[ClH:23]>C(O)(C)C.O>[ClH:23].[C:1]([NH:5][CH:6]1[CH2:10][C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:8]=[CH:7]1)([CH3:4])([CH3:2])[CH3:3]This amine was suspended in a mixture of isopropyl alcohol (0.4 ml) and water (0.2 ml). To the suspension was added conc. hydrochloric acid (0.065 ml) in an ice bath, and the mixture was stirred for 5 hours. The resulting precipitates were collected by filtration, washed with 30% aqueous isopropyl alcohol (0.4 ml), and dried to give (-)-N-t-butyl-4,4-diphenyl-2-cyclopentenylamine hydrochloride (89 mg).
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