Ethyl chloroformate → HCID 22750666, compound

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Reaction Steps

12.2 g. of 1-methyl-10,11-dihydro-5-(3-dimethylaminopropyl)-5H-dibenzo[a,d]cycloheptene, dissolved in 180 ml. of dry benzene, are added dropwise to a mixture of 13.6 g. of ethyl chloroformate and 50 ml. of dry benzene. The mixture is boiled and stirred under reflux for 20 hours. After cooling, the benzene solution is washed with dilute hydrochloric acid and water and evaporated. The residual 1-methyl-10,11-dihydro-5-(3-methylcarbethoxyaminopropyl)-5H-dibenzo[a,d]cycloheptene distils at 180° C./0.01 mmHg. 10.6 g. of 1-methyl-10,11-dihydro-5-(3-methylcarbethoxyaminopropyl)5H-dibenzo[a,d]cycloheptene, 12.6 g. of potassium hydroxide and 110 ml. of n-butanol are boiled at reflux for 20 hours under an atmosphere of nitrogen with strong stirring. The butanol is removed by distillation under reduced pressure. The residue is taken up in ether and the ethereal solution shaken with dilute hydrochloric acid. By treatment of the aqueous acidic phase with excess potassium carbonate, 1-methyl-10,11-dihydro-5-(3-methylaminopropyl)-5H-dibenzo[a,d]cycloheptene separates out as an oil which distils at 150° C. under 0.01 mmHg. After recrystallization from ethanol-ether, the hydrochloride has a melting point of 173°-175° C.

Provenance & Evidence