Sodium hydride → N-(2-Dimethylaminoethyl)-N-(5-methyl-2-pyridyl)acetamide

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Reaction Steps

N-(5-Methyl-2-pyridyl)acetamide (75.0 g, 0.5 mole) is dissolved in 1000 ml of dry dimethylformamide and a 50% suspension of sodium hydride in mineral oil (24.0 g, 0.5 mole) is added under nitrogen with stirring in two portions over 1/2 hour. The temperature rises to 40° and then is increased to 50°-55° to keep the salt in addition. Additional sodium hydride suspension (28.8 g, 0.6 mole) is added over 10 minutes followed by 2-dimethylaminoethyl chloride hydrochloride (86.5 g, 0.6 mole) added in small portions over 1/2 hour. The temperature is moderated at 70° with occasional ice bath cooling. Then the mixture is stirred overnight at steam bath temperature. The reaction mixture is cooled and filtered. Removal of the dimethylformamide under reduced pressures gives a dark liquid. The product distills as a pale yellow liquid at 124°-128° at 0.6 mm, n25D 1.5216. Weight obtained is 78 g.

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