[H-].[Na+].[Br:3][C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[CH2:6][NH:7][CH:8]1[CH2:10][CH2:9]1.I[CH3:16].Cl>O1CCCC1>[Br:3][C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[CH2:6][NH:7][CH2:8][CH:10]1[CH2:9][CH2:16]153 mg of sodium hydride in 3 ml of tetrahydrofuran are added to 300 mg of (2-bromobenzyl)cyclopropylamine in 2 ml of tetrahydrofuran with ice-cooling. 207 μl of iodomethane are subsequently added, and the mixture is heated at 600 for 1 h. The mixture is allowed to cool and poured onto 20 g of ice and 5 ml of 1N hydrochloric acid, washed 4 times with 10 ml of ethyl acetate each time, and the combined organic phases are dried over sodium sulfate. After filtration, the filtrate is evaporated to dryness.
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