C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]Br.[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2([NH2:28])[CH2:26][CH:25]3[CH2:27][CH:22]2[CH2:23][CH2:24]3)=[CH:17][CH:16]=1>CN(C=O)C>[F:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2([N:28]3[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]3)[CH2:26][CH:25]3[CH2:27][CH:22]2[CH2:23][CH2:24]3)=[CH:19][CH:20]=1Anhydrous potassium carbonate (0.94 g, 6.8 mmol) and 1,5-dibromopentane (0.47 ml, 3.4 mmol) were added to a crude base of (±)2-(4-fluoro-phenyl)-bicyclo[2.2.1]hept-2-ylamine (compound 2; Table 1) (0.70 g, 3.4 mmol) in dry DMF (30 ml). The mixture was heated to 50° C. and incubated for 8 hours. The mixture was then stirred overnight at room temperature and subsequently quenched with water. The resultant mixture was extracted with chloroform (3×20 ml). The chloroform extracts were combined and the chloroform was removed using a rotary evaporator. The remaining residue was extracted with ether (2×25 ml), and the ethereal extract was washed with water (2×20 ml) and dried over anhydrous sodium sulfate. A pale yellow oil was obtained after removing the ether. Purification by TLC with a mobile phase of chloroform and diethyl ether (9:1) resulted in a colorless crystalline compound (0.65 g, 70% yield, m.p. 58-59° C.).
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