[2-Dimethylamino-6-methoxybenzothien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone → 4-(2-(Piperidin-1-yl)ethoxy)benzaldehyde

Participants

Reaction Steps

Add a solution of 2-methoxybenzylmagnesium chloride (5 mL of 0.25 M/THF) to a stirred solution of (2-dimethylamino-6-methoxy-benzo[b]thiophen-3-yl)-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (500 mg, 1.14 mmol) in THF (5 mL) at −78° C. After 30 min, add additional 2-methoxybenzyl-magnesium chloride (5 mL). After 30 min, quench with water and dilute with iPrOH/CHCl3(1:3). Wash the organic phase with water and brine, dry over MgSO4, filter and concentrate to yield 6-methoxy-2-(2-methoxy-benzyl)-benzo[b]thiophen-3-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (686 mg). Use the crude product without further purification.

Provenance & Evidence