N-Ethyl-N-4-piperidinylacetamide → HCID 19761220, compound
Reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]([CH2:11][CH3:12])[C:8](=[O:10])[CH3:9])[CH2:3][CH2:2]1.S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH3:24][CH:25]1[C:28]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:27]2[CH2:26]1>C1(C)C=CC=CC=1>[C:25]1([CH2:24][N:1]2[CH2:6][CH2:5][CH:4]([N:7]([CH2:11][CH3:12])[C:8](=[O:10])[CH3:9])[CH2:3][CH2:2]2)[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[CH:26]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3.3 g of N-piperid-4-yl-N-ethylacetamide and 2.8 g of 1-methylbenzocyclobutene tosylate (prepared in accordance with the process described in J.A.C.S., (1975), 154, p. 347) are refluxed under nitrogen for 20 hours in 16 ml of toluene. After cooling, the reaction mixture is evaporated to dryness and taken up in diethyl ether. After extraction with N hydrochloric acid, the extract is rendered basic in the presence of diethyl ether and the organic phase is washed with water, dried over magnesium sulphate and evaporated in vacuo to yield N-[1-(benzocyclobuten-1-ylmethyl)-piperid-4-yl]-N-ethylacetamide. The corresponding hydrochloride is obtained in ethyl acetate in the presence of ethereal hydrogen chloride.