Acetic Acid → 2-Methyl-5-phenylpentan-2-amine

Participants

Reaction Steps

A 1008 g quantity of N-(1,1-dimethyl-4-phenylbutyl)-2-chloroacetamide (3.98 moles) was dissolved in 8.4 L of ethanol and 1080 mL gl. acetic acid in a 22 L 3-necked, round-bottomed flask equipped with stirrer, thermometer and reflux condenser and 370 g (4.86 moles) of thiourea was added. The reaction was heated to reflux to dissolve the thiourea. A white crystalline precipitate began to form after about two hours of reflux. The reflux was continued for additional 8 h. The reaction mixture was allowed to cool to ambient temperature and was filtered and the filtrate diluted with 8 L of water, extracted with 2×1 L of hexane and neutralized by the addition of 220 mL 50% sodium hydroxide. This caused an oil to form which was separated and the aqueous phase extracted with 2×2 L of ether/hexane. The extracts were combined with the oil and concentrated to give 590 g of reddish oil, LC/MS single peak, m/e 179, NMR (CDCl3) consistent with the desired product, 1,1-Dimethyl-4-phenylbutylamine, 84% crude yield. This material was vacuum distilled to give 518 g of clear oil, bp(1 torr) 71-74°.

Provenance & Evidence