Dichloromethane → 3-(3-Methyl-2-octyl)-1-[4-(piperidino)butyryloxy]-6,6,9-trimethyl-7,8,9,10-tetrahydro-6H-dibenzo[b,d]pyran hydrochloride

Participants

Reaction Steps

2.5 g. (6.76 mmole) of 1-Hydroxy-3-(3-methyl-2-octyl)-6,6,9-trimethyl-7,8,9,10-tetrahydro-6H-dibenzo[b,d]pyran was combined with 1.41 g. (6.76 mmole) of γ-piperidinobutyric acid hydrochloride and 1.48 g. (7.16 mmole) of dicyclohexylcarbodiimide in 125 ml. of methylene chloride and stirred at room temperature for 16 hours. The by-product of dicyclohexylurea was removed by filtration and the filtrate was evaporated to give a light brown residue. The residue was dissolved in ether and the small amount of solid which appeared was removed by filtration. The ether was removed on a rotary evaporator and the gummy residue which remained was triturated several times with small quantities of hexane. The material was thoroughly dried to give 2.8 g. (74%) of product as a colorless powder. The material was pure by thin layer chromatography (10% MeOH/CHCl3); the infrared and nmr spectra are consistent with the desired product.

Provenance & Evidence