Butyl bromide → 1-Butyl-2,2,6,6-tetramethylpiperidin-4-ol

Participants

Reaction Conditions

Reaction Steps

Into a 400-milliliter Hastalloy pressure tube are placed 62.8 grams of 2, 2, 6, 6-tetramethyl-4-hydroxypiperidine and 35.6 grams of 1-bromobutane. The tube and contents are cooled to -78°C., evacuated and filled with nitrogen. The tube is sealed, shaken and warmed to 100°C. for 1 hour, 120°C. for 1 hour and 150°C. for 30 hours. The tube is cooled and the solid charge is removed and placed in a Sohlet extraction apparatus. The material is extracted for 8 hours with diethyl ether. The resulting ether solution is treated with activated charcoal, filtered and concentrated under vacuum. The residue is distilled at 120°-125°C. at 1 torr to give 26 grams of 1-(1-butyl)-2, 2, 6, 6-tetramethyl-4-hydroxypiperidine, a white solid melting at 29°-33°C.

Provenance & Evidence