1-Bromohexane → HCID 23000911, compound

Participants

Reaction Conditions

Reaction Steps

To 4-(3-hydroxyphenyl)-4-n-propylpiperidine (Preparation 67, 1.10 g, 5.0 mmol) in N,N-dimethylformamide (25 ml) was added sodium hydrogen carbonate (462 mg, 5.5 mmol) and 1-bromohexane (0.77 ml, 5.5 mmol). The reaction mixture was heated at 100° C. for 3 h 30 min and then allowed to cool to room temperature. The mixture was diluted with water (25 ml) and extracted with dichloromethane (3×25 ml). The combined extracts were washed with water (20 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by (50 g) silica column chromatography eluting with ethyl acetate:hexane:0.880 ammonia (40:60:1) to give the title compound as a pale yellow oil (1.17 g, 77%).

Provenance & Evidence