Hydrochloric Acid → 4,4-Dimethyl-7-(3-methyl-2-octyl)-9-[3-(piperidino)-propionyloxy]-1,2,3,4-tetrahydrocyclopenta[c][1]-benzopyran hydrochloride

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Reaction Steps

2.8 g. (8.2 mmoles) of 4,4-dimethyl-9-hydroxy-7-(3-methyl-2-octyl)-1,2,3,4-tetrahydrocyclopenta[c] [l] benzopyran, 1.77 g. (8.6 mmoles) of dicyclohexylcarbodiimide and 1.65 g. (8.5 mmoles) of β-piperidinopropionic acid hydrochloride (m.p. 216°-220°, J. Am. Chem. Soc. 73, 3168 (1951)) were combined with 125 ml. of methylene chloride and stirred at room temperature for about 20 hours. The reaction mixture was filtered and the methylene chloride removed using a rotary evaporator. The residue was treated with benzene and filtered to remove a small quantity of insoluble material. The benzene was evaporated and the dark viscous residue was chromatographed using 100 g. of 60-100 mesh Florisil activated magnesium silicate and methanol/chloroform graded solvent mixtures. Chromatography gave a small quantity of orange oil which was dissolved in ether and treated with a solution of ethereal HCl. The desired compound appeared as white crystals which were filtered and washed with additional ether. The colorless crystals (86 mg., m.p. 106°-107°) were pure by thin layer chromatography (10% MeOH/CHCl3) and the nmr and infrared spectra are in agreement with the proposed structure.

Provenance & Evidence