ketobemidone

Chemical properties

ketobemidone is white or almost white, crystalline powder.

Originator

Ketobemidone,Shanghai Lancheng Corporation

The Uses of ketobemidone

ketobemidone is an opioid analgesic. Used as a substitute to morphine for postoperative pain in children.

Definition

ChEBI: Ketobemidone is a member of piperidines.

Manufacturing Process

The process includes the following steps:
1. 80 weight parts (w.p.) powder of sodium amide was added to 147 w.p. 3- methoxy-benzylcyanide, 156 w.p. N,N-bis(2-chloroethyl)-N-methylamine and 350 w.p. toluene in 6-8 portions by stirring at 40°-45°C. The mixture was slowly heated to 100°-105°C with stirring for 1 hour at this temperature. Some water was added after cooling, the toluene layer was treated with diluted HCl and it therefrom was adjusted to a alkaline pH by addition of sodium hydroxide, extracted with ether and the ether layer dried over Na2CO3. The solvent was removed; the distillation of the residue gave 4-cyan- 4-(3-metoxyphenyl)-1-methylpiperidine as a colorless oil; BP 150°C at 2 mm/Hg, hardened by standing; MP 44°C. The yield was 65-68%.
2. The solution of ethyl magnesium bromide from 36 w.p. magnesium and 165 w.p. ethyl bromide in 700 w.p. ether was added to 230 w.p. above cyanide in 330 w.p toluene. The mixture was refluxed for 1 hour. Then the ether was slowly distilled and the residue was stood for 1 hour at water bath temperature. After cooling with an ice the mixture was acidified by addition of HCl to adjust the congo acid pH. 4-(3-Methoxyphenyl-1-methyl-4- propipnylpiperidine was prepared by a saturation of above solution with NH3 and it therefrom was dried over K2CO3 and distilled to give a colorless product BP 184°-185°C at 6 mm/Hg.
3. The mixture 261 w.p 4-(3-methoxyphenyl)-1-methyl-4-propipnylpiperidine and 750 w.p. HBr (BP 126°C) was refluxed for 1 hour. Then 2/3 of acid was distilled on an oil bath and the hot water was added to the rest. The title product was precipitated by NH3 as the oil that became hard and after recrystallisation from ethylacetate had MP 156°-157°C.

Therapeutic Function

Narcotic analgesic