Triethylamine → 5-[4-{5-(5-Methyl-1,3,4-oxadiazol-2-yl)-1-naphthyl}benzoyl]-1'-methyl-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine]hydrochloride

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Reaction Steps

1-(4-Carboxyphenyl)-5-(5-methyl-1,3,4-oxadiazol-2-yl)naphthalene (D4) (0.49 g, 0.45 mmol) in dichloromethane was treated with oxalyl chloride (0.047 ml, 0.53 mmol) followed by 1 drop of DMF. This mixture was stirred under Ar for 1 h, washed with potassium carbonate/brine solution, dried (Na2SO4) and evaporated to give a white solid. This was redissolved in dichloromethane (10 ml), and treated with 1'-methyl-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine (D8 in WO 96/19477, 0.100 g, 0.41 mmol) and triethylamine (0.09 ml, 0.65 mmol). The mixture was stirred for 1 h, washed with potassium carbonate/brine solution, dried (Na2SO4) and evaporated. The crude material was purified by chromatography on silica gel, eluting with 0-10% methanol/dichloromethane. This gave the free base of the title compound (0.154 g, 67%) as white solid. This was dissolved in dichloromethane, treated with 1M HCl in ether

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