Sulfuric Acid → 5-(2-dimethylaminoethyl)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carbaldehyde

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Reaction Conditions

Reaction Steps

To a solution of 5-(2-dimethylaminoethyl)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile (101) (4.15 g, 14.3 mmol) in 50 mL of CH2Cl2 stirred at −78° C. and maintained under a nitrogen atmosphere was added diisobutylaluminum hydride (20.6 mL of a 1.0M solution in CH2Cl2; 20.6 mmol) dropwise. The mixture was stirred at −78° C. for 30 minutes, warmed to 0° C. and left stir an additional 4 hours. The solution was poured into 35 mL of saturated aqueous ammonium chloride. The resulting gelatinous mixture was stirred vigorously for 15 minutes, then 65 mL of 1.5N sulfuric acid was added and the mixture stirred overnight. The mixture was extracted with CH2Cl2 (3×), and the combined organic layers were washed with saturated aqueous sodium bicarbonate and brine, dried the over sodium sulfate, filtered, and evaporated do dryness. The resulting oil was purified by chromatography on silica gel with 96/4/0.4 of methylene cloride/methanol/ammonium hydroxide. The product fractions were evaporated to dryness to yield the title product as an oil.

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