N-Ethyl-3-chloropiperidine

N-Ethyl-3-chloropiperidine Benzilic acid Methyl bromide... 

N-ethyl-3-chloropiperidine was prepared according to the method of Fuson and Zirkle described in Volume 70, J. Am. them. Soc., p 2760. 12.0 g (0.0B1 mol) of N-ethyl-3-chloropiperidine was mixed with 1B.6 g (0.0B1 mol) of benzilic acid and 80 cc of anhydrous isopropyl alcohol as a solvent. The mixture was refluxed for 72 hours. The solution was then filtered and concentrated at 30 mm of mercury. The concentrate was dissolved in water, acidified with hydrochloric acid and extracted with ether to remove the unreacted benzilic acid. 

N-Ethyl-3-chloropiperidine Pipenzolate bromide 1 -Ethyl-3-chloropyrrolidine Doxapram HCI Ethyl -chlorovinyl ketone Ethchlorvynol Ethyl cyanoacetate Ethosuximide Piprozolin Tinoridine... 

Preparation of 4-aza-S-(N-methyl-4-piperidyll-10,11-dihydro-SH-dibenzo[a,d]cycloheptene-S-ol Add 17.4 g of N-methyl-4-chloropiperidine to a stirred mixture containing 3.2 g of magnesium, 20 ml of anhydrous tetrahydrofuran, 1 ml of ethyl bromide and a crystal of iodine. Reflux for two hours, cool to 30°-35°C and add a solution of 13 g of 4-aza-10,11 -dihydro-5H-dibenzo[a,d] cycloheptene-5-one in 25 ml of tetrahydrofuran. Stir for five hours, remove the solvent by distillation in vacuo and add 250 ml of ether. Add 100 ml of 10% ammonium chloride solution and extract the mixture with chloroform. Concentrate the chloroform solution to a residue and recrystallize from isopropyl ether obtaining 20 g of the carbinol,... 

Ethyl l-azabicyclo[3.1.0]hexane-5-carboxylate 6 with hydrochloric acid gives 3-chloropiperidine-3-carboxylic acid hydrochloride 53 by ring opening with concomitant hydrolysis. Catalytic reduction with hydrogen over palladium on charcoal causes cleavage of both aziridine N—C bonds of the parent azabicyclohexane 1, to give 2-methylpyrrolidine (54) and piperidine (55) in the ratio 2 1. ... 

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