Ammonia → HCID 3045754, compound

Participants

Reaction Steps

0.73 g of n-caproyl chloride is added to a mixture of 0.5 g of 1-(3-hydroxyphenyl)-6-azabicyclo[3,2,1]octane, 0.62 g of triethylamine and 10 ml of dimethylformamide. The mixture is stirred at room temperature for 4 hours. Then, water is added to the mixture, and the aqueous mixture is extracted with chloroform. The chloroform extract is washed with water, dried and then evaporated to remove solvent. The residue thus obtained is dissolved in 40 ml of tetrahydrofuran. 0.9 g of lithium aluminium hydride is added to the solution, and the solution is refluxed for 12 hours under heating. After cooling, water is added to the reaction solution to decompose lithium aluminium hydride. The reaction solution is acidified with hydrochloric acid. Then, the reaction solution is made alkaline with aqueous ammonia and extracted with chloroform. The chloroform extract is washed with water, dried and then evaporated to remove solvent. The residue is dissolved in 5 ml of chloroform. The chloroform solution is poured onto the column of 50 g of silica gel. Then, the column is eluted with a mixture of 950 ml of chloroform and 50 ml of methanol, and the effluent is evaporated to remove solvent. The residue thus obtained is distilled under reduced pressure, whereby 0.48 g of 1-(3-hydroxyphenyl)-6-n-hexyl-6-azabicyclo[3,2,1]octane is obtained as a viscous oil boiling at 250°C(bath temperature/0.1 mmHg.

Provenance & Evidence