4-Methoxy-4-(1-methylethyl)piperidine → HCID 20373715, compound

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:14])[CH2:9][CH2:10][C:11]([Cl:13])=O)=[CH:4][CH:3]=1.[CH:15]([C:18]1([O:24][CH3:25])[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)([CH3:17])[CH3:16]>C1C=CC=CC=1.C(N(CC)CC)C>[ClH:13].[CH:15]([C:18]1([O:24][CH3:25])[CH2:19][CH2:20][N:21]([CH2:11][CH2:10][CH2:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[O:14])[CH2:22][CH2:23]1)([CH3:17])[CH3:16]

Participants

Procedure

To a mixture of 21.5 g (0.1 m) of gamma-(p-fluorophenyl)-gamma-oxo-butyric acid chloride and 15.7 (0.1 m) of 4-isopropyl-4-methoxy-piperidine in 200 ml of benzene, 15.5 ml (0.11 m) of triethylamine is added. The triethylamine hydrochloride formed is filtered off and the solvent removed by evaporation under vacuum on a steambath. The residue is dissolved in dry ether and added dropwise to a suspension of 15 g of lithium aluminum hydride in ether. The reaction mixture is refluxed for two hours and the obtained mixture decomposed with water. The precipitate is filtered off and the ether solution evaporated. The residue, which consists of the alcohol corresponding to the butyrophenone, is oxidized according to Oppenauer with 60 g of aluminum-isopropylate in 500 ml of dry acetone. The reaction mixture is refluxed for 12 hours, cooled, and decomposed with water. After centrifugation, the solution is evaporated to dryness, whereafter the residue dissolved in ether and the hydrochloride precipitated with alcoholic hydrochloric acid. After recrystallization, the hydrochloride melts at 190°-192° C. Yield 19 g. The tartrate is prepared using tartaric acid.