Sodium Carbonate → (s)-n-[2-(2,3,-Dihydrobenzofuran-5-yl)-1-methylethyl]-n-ethyl-(1-methanesulfonylpiperidin-4-ylmethyl)amine

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Reaction Steps

(S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]ethylamine (24 grams, 0.117 mole) was dissolved in dichloroethane (300 ml) and sodium triacetoxyborohydride (37.2 grams, 0.176 mole) was added. After stirring for 5 minutes N-methanesulfonylpiperidine-4-carboxaldehyde (22.4 grams, 0.117 mole) was added and the mixture was stirred for another 2 hours. 5% sodium carbonate (600 ml) was added and the mixture was extracted with dichloromethane. Evaporation of the solvent gave an oil which was recrystallized from ether to give (S)-N-[2-(2,3,-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(1-methanesulfonylpiperidin-4-ylmethyl)amine (28 grams, 63%), m.p. 99-101° C.

Provenance & Evidence