Acetic Acid → HCID 19102631, compound

Participants

Reaction Steps

NaCNBH3 (6.4 g, 101.8 mmol) was added to a stirred solution of 5-(1-ethoxyethoxy)-4-formyl-1,3-benzodioxole (16.0 g, 67.2 mmol) and 1-methylpiperazine (20.2 g, 201.7 mmol) in CH3CN (150 ml). Acetic acid (10 ml) was added dropwise to the solution in one hour at room temperature, to keep the pH neutral (pH=7). After 3 hours of additional stirring, most of the CH3CN was evaporated in vacuo. Aqueous NaOH (2N, 300 ml) was added and the resulting mixture was extracted with diethyl ether (3 times). The combined ether extracts were washed with an aqueous solution of Na2CO3, dried over Na2SO4, filtered and evaporated to yield 26 g of a crude oil. This oil was purified by flash chromatography (eluent gradient; dichloromethane/methanol/25% aqueous ammonia=95/4.5/0.5 to 85/14/1 (v/v) to give 5-(1-ethoxyethoxy)-4-(4-methyl-piperazinylmethyl)-1,3-benzodioxole (16.0 g, 74% yield, compound No. 4) as a colorless oil.

Provenance & Evidence