Dichloromethane → 4-{[3-(3-Benzyl-3,8-diazabicyclo[3.2.1]oct-8-yl)propyl]amino}benzonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-benzyl-3,8-diazabicyclo[3.2.1]octane (3.63 g, 17.9 mmol; from Preparation B, step (e) above), 3-(4-cyanoanilino)propyl 4-methylbenzenesulfonate (5.93 g, 17.9 mmol; from step (b) above) and potassium carbonate (2.47 g, 17.9 mmol) in dry DMF (85 mL) was stirred at 80° C. for 4 h. The reaction mixture was diluted with water (200 mL) and extracted with ether (4×200 mL). The combined extracts were washed with brine, dried (Na2SO4), filtered and concentrated ill vacuo to give the crude product. Flash chromatography on silica gel eluting with CH2Cl2:CMA (4:1) gave 6.26 g (97%) of the sub-title compound as a yellow oil.

Provenance & Evidence