Benzene → Kabi 2023

Participants

Reaction Steps

Phosgene (1 g) is added to dimethylamino-1-[spiro(cyclopentane-1,1'-indene)-3'-yl]ethanol (2.9 g) in benzene (25 ml). The mixture is stirred at room temperature for 30 minutes and then under reflux for 2 hours. Evaporation of the solvent under reduced pressure gives an oil which crystallizes. Recrystallization from diisopropyl ether gives a pure product, m.p. 75°-77° C. This compound, 5-[spiro(cyclopentane-1,1'-indene)-3'-yl]ethanol (2 g), is refluxed for 2 hours with a solution of potassium hydroxide (5 g) in ethanol (50 ml) and water (10 ml). Most of the solvent is evaporated under reduced pressure, water (25 ml) is added and the amine is extracted into chloroform. Drying and evaporation of the solvent gives the crystalline title compound, which after recrystallization from diisopropyl ether melts at 133°-134° C.

Provenance & Evidence