The Gomberg—Bachmann Reaction with Benzene-d

Distillation of the product gave 0.66-g.forerun, b.p. 42-50° (6 mm.), identical in infrared spectrum with benzylamine, and 4.05 g. (67%) of 5-benzylamino-l-pentanol, b.p. 152-168° (6 mm.), lit.4 b.p. 174-178° (11 mm.).The infrared spectrum was com- patible with the assigned structure.5-Piperidino-l-pentanol from Pentamethylene Chlorohydrin.-Ina 250-ml.three-necked flask equipped with a condenser, mag- netic stirrer, dropping funnel, and thermometer were placed 25.5 g. (0.3 mole) of piperidine and a pellet of potassium hydroxide in 100 ml. of water.Pentamethylene chlorohydrin (13.9 g., 0.1 mole) was added dropwise at room temperature.The mixture was then heated at about 78° for 2 hr. and cooled.Potassium hydroxide pellets were added until two layers formed.These were separated, and the aqueous layer was extracted with three 100-ml.portions of diethyl ether.The ether extracts were com- bined with the original organic material, dried over potassium carbonate, and concentrated.Distillation at 175 mm.led to removal of excess piperidine.The residue distilled at 100-112° (5.5 mm.), n18n 1.4799, and weighed 12.7 g. (74%); lit.7 b.p. 140° (13 mm.), n16,6D 1.4820.