Sodium Carbonate → HCID 18784691, compound

Participants

Reaction Steps

A stirred solution of 5-(2'-methyl-4'-(5-methyl-1,3,4-oxadiazol-2-yl)biphenyl-4-carbonyl)-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine] (E17 in WO 96/19477, 500 mg, 0.99 mmole) in ethanol (40 ml) was treated with sodium carbonate (419 mg, 3.9 mmole) and 2-dimethylaminoethyl chloride hydrochloride (287 mg, 1.98 mmole) and heated under reflux for 48 hours. The reaction mixture was concentrated in vacuo and the residue treated with 10% Na2CO3 solution and extracted with ethyl acetate. The extract was dried (Na2SO4), concentrated in vacuo and the residue chromatographed on silica gel eluting with 0-8% methanol/chloroform to afford the title compound as a yellow/beige solid (75 mg, 13%). This was converted to its hydrochloride salt and crystallised from acetone/ether m.p. 246-248° C.

Provenance & Evidence