Methanol → alpha-Nicotine

Participants

Reaction Steps

2-Pyridinyl phenoxazine (46 mg,), 2-(2-aminoethyl)-1-methylpyrrolidine (20 ul, 0.13 mmol) and aluminum chloride (21 mg, 0.1575 mmol) were mixed in anhydrous dichloromethane (1 ml) and stirred for 1 h. The mixture was then evaporated to a residue which was washed with saturated aqueous sodium potassium tartaric acid. The mixture was then extracted with 3×10 ml dichloromethane and the extracts dried (Na2SO4) and evaporated. The compound was then isolated using preparative thin layer chromatography (Al2O3, 3% MeOH in dichloromethane) to yield the 2-pyridinyl methylpyrollidine (25 mg) as a yellow solid.

Provenance & Evidence