Dichloromethane → (+,-)-1-[(2-Methoxyphenyl)methyl]-3-phenyl-piperazine, dihydrochloride salt

Participants

Reaction Conditions

Reaction Steps

To a solution of (+,-)-2-phenyl-piperazine (2.83 g, 17.44 mmol) (described in Example 1) in dry CH2Cl2 (141.5 mL) at -78° C. was added slowly a solution of 1-bromomethyl-2-methoxy-benzene (3.507 g, 17.44 mmol) in dry CH2Cl2 (35 mL) under nitrogen. The reaction was stirred at -78° C. and gradually warmed to RT overnight. After completion, the product was diluted with CH2Cl2 (200 mL), washed with brine (100 mL), dried over MgSO4 and filtered. The filtrate was removed under vacuum to give an oil. The product was purified by flash chromatography on flash grade silica gel (150 g), eluting with 4% MeOH/CH2Cl2 to give the title compound as an oil (2.68 gram, 54%). A portion of this oil (0.33 g, 1.168 mmol) was dissolved in CH2Cl2 (10.0 mL) and treated with 2.3M HCl (1.1 mL, 2.53 mol). After stirring at room temperature for 10 minutes, solvents were removed under vacuum to give a solid, m.p. 152°-156° C.; FAB MS [M+1]+ 283.2.

Provenance & Evidence