Bicyclo(2.2.1)hept-5-ene-2-carboxaldehyde → 1-Bicyclo[2.2.1]hept-5-en-2-ylmethyl-4-(5-chloro-2-methoxy-phenyl)-2-methyl-piperazine

Beteiligte Stoffe

Reaktionsschritte

48 mg (0.2 mmol) of 1-(5-Chloro-2-methoxy-phenyl)-3-methyl-piperazine was dissolved in 1.5 mL anhydrous 1,2-dichloroethane. 5-Norbornene-2-carboxaldehyde (25 mg, 0.2 mmol) was added, followed by followed by 63 mg (0.3 mmol) sodium triacetoxyborohydride [NaBH(OAc)3]. The reaction was stirred overnight, then quenched with 1.0 mL DMSO:methanol (1:1). The reaction mixture was filtered and purified by reverse-phase HPLC (2-99CH3CN in 0.085% TFA (aq), 50 mL/min, 2.0 mL injected), and the product 1-bicyclo[2.2.1]hept-5-en-2-ylmethyl-4-(5-chloro-2-methoxy-phenyl)-2-methyl-piperazine isolated as the mono-TFA salt. Theoretical (M+H)+ m/z=347.9; Found 348.0.

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