[NH4+:1].[Cl-].C[Al](C)C.[Br:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2([CH2:19][C:20]#[N:21])[CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2([CH2:19][C:20]([NH2:1])=[NH:21])[CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:12][CH:13]=1
To a suspension of NH4Cl (1.21 g, 43.65 mmol) in toluene (30 mL) was added dropwise a solution of trimethyl aluminium (1.64 g, 43.65 mmol, 2M in toluene) at 0° C. and stirred for 2 h at room temperature prior to the addition of a solution of [1-(4-bromophenyl)-cyclopentyl]-acetonitrile (228) (2.0 g, 7.57 mmol) in toluene (10 mL). The resulting solution was heated to 80° C. for 16 h. The cooled reaction mixture was poured into a slurry of silica gel (10 g) in CHCl3 (20 mL), followed by vigorous stirring for 30 min. The silica gel was filtered off and the cake was rinsed in turn with methanol. The solvent was evaporated and the crude product was taken up in 10% methanol in dichloromethane (200 mL) and stirred for 30 min. The solid suspension was removed by filtration and the filtrate was evaporated. The crude product was triturated in diethyl ether and the solid was collected by filtration and dried under vacuum to afford HCl-salt of 2-[1-(4-bromophenyl)-cyclopentyl]-acetamidine (229) (1.78 g, 74%) as a white solid.
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