Butyl iodide → 1-(6-Amino-2-methoxy-3-pyridinyl)-3-(1-butyl-4-piperidinyl)-1-propanone

Participants

Reaction Steps

A mixture of 1-(6-amino-2-methoxy-3-pyridinyl)-3-(4-piperidinyl)-1-propanone (step 1, 175 mg, 0.665 mmol), 1-iodobutane (0.083 ml, 0.732 mmol) and potassium carbonate (184 mg, 1.33 mmol) in tetrahydrofuran (5 ml) was refluxed for 6 h. After cooling to room temperature, the mixture was diluted with ethyl acetate (50 ml), washed with water (5 ml) and brine (10 ml) and dried over potassium carbonate. Removal of solvent gave the pale yellow oil, which was chromatographed on a column of silica gel eluting with 25% ammonium hydroxide/methanol/dichloromethane (0.2:1:10) to give pale yellow solid, which was washed with acetonitrile to afford 107.0 mg (50%) of the title compound as pale yellow solids.

Provenance & Evidence