4-Methylmorpholine → 4-(8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyrid-11-ylidene)-1-[4-(2-methylimidazo[4,5-c]pyrid-1-yl)benzoyl]piperidine hemihydrate

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A solution of 4-(8-chloro-5,6-dihydro-11-H-benzo[5,6]cyclohepta[1,2-b]pyrid-11-ylidene-piperidine (224 mg, 0.75 mmol) and (4-(2-methylimidazo[4,5-c]pyrid-1-yl)benzoic acid (190 mg, 0.75 mmol) in dichloromethane (12 ml) was treated sequentially with 1-hydroxybenzotriazole hydrate (102 mg, 0.75 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (290 mg, 1.5 mmol) and 4-methylmorpholine (165 μl; 1.5 mmol). The mixture was stirred at room temperature for 16 hours, washed with water, dried over magnesium sulphate and evaporated. The residue was purified by chromatography on silica using dichloromethane plus 3-4% methanol as eluant. Appropriate fractions were combined and evaporated to give the title compound (113 mg, 27%) as a colourless foam which was characterised as a hemihydrate. Found: C,71.1; H,5.2; N,12.3. C33H28ClN5O. 0.5 H2O requires C,71.4; H,5.3; N,12.6%.

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