Isopropanol → alpha-Amino-5H-dibenzo[a,d]-cycloheptene-5-acetic acid, hydrochloride

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Reaction Steps

Ethyl α-amino-5H-dibenzo[a,d]cycloheptene-5-acetate, hydrochloride (0.21 g, 0.6 mmol) dissolved in 10 mL of absolute ethanol is stirred with 3 mL of 1.25M ethanolic potassium hydroxide solution until TLC (SiO2, hexane:2-propanol/3:1) shows no starting material (2 hours). The solvent is stripped and a residual solid is taken up in water and extracted with dichloromethane. The aqueous layer is acidified with 6N hydrochloric acid to pH 1 and stripped to dryness. The residue is treated with 5 mL of boiling water, cooled to room temperature, then refrigerated overnight. A solid is collected, washed with diethyl ether (0.05 g); mp 225° C. (dec).

Provenance & Evidence