Potassium Carbonate → 1-(Benzothiazol-2-yl)-3-(SR)-((4-phenyl)piperidin-1-yl)methyl-4-(SR)-phenylpyrrolidine

Participants

Reaction Conditions

Reaction Steps

A mixture of 54 mg (0.16 mmol) of 3-(SR)-((4-phenyl)piperidin-1-yl)methyl-4-(SR)-phenylpyrrolidine (from Example 30, Step A), 53 mg (0.31 mmol) of (2-chloro)benzothiazole and 65 mg (0.47 mmol) of K2CO3 in 3 mL of DMF was heated at 80° C. for 1 h. The reaction mixture was cooled, partitioned between 25 mL of ether and 15 mL of H2O and the layers were separated. The organic layer was dried over MgSO4 and concentrated in vacuo. Flash chromatography on 15 g of silica gel using 1:1 v/v hexnaes/EtOAc as the eluant afforded 16 mg (23%) of the title compound as an oil. 1H NMR (500 MHz, CDCl3): δ1.79-3.04 (12H), 3.29 (q, J=8.9, 1H), 3.55 (t, J=9.0, 1H), 3.69 (t, J=9.6, 1H), 4.03-4.11 (m, 2H), 7.07-7.64 (14H). Mass Spectrum (NH3 -CI): 454 (M+.1).

Provenance & Evidence