Proton sponge → HCID 19045570, compound

Participants

Reaction Steps

To a solution of 6,7-dimethoxy-1'-methylspiro[1,2,3,4-tetrahydroisoquinoline-1,4'-piperidin]-4-one (Helv. Chem. Acta., 588, Fasc. 1, Nr. 8 (1975)) (1.0 g) and N,N,N',N'-tetramethyl-1,8-napthalenediamine (0.9 g) in dichloroethane at 0° C. under nitrogen was added 1-chloroethyl chloroformate (9.5 ml) and the mixture stirred at reflux for 1 hr. The reaction was cooled, passed thru silica and the product eluted with 10% ethyl acetate in methylene chloride. After evaporation, methanol was added and the mixture refluxed for 1 hr. Upon evaporation the foam was crystallized from ethanol/ether to give 0.6 g of the title compound as dihydrochloride salt.

Provenance & Evidence