Hydrochloric Acid → HCID 18333131, compound

Participants

Reaction Steps

3-(N-Benzyl-N-methylamino)methyl-1-[3-(4-biphenylyl]propanoyl)-1,2,3,4-tetrahydroquinoline oxalate (0.800 g) was converted into a free form, which was dissolved in THF (5 ml). 1M Borane-THF complex (3 ml) was added to the reaction mixture, which was heated under reflux for 30 minutes, then left standing for cooling. Water (0.5 ml) and 6N hydrochloric acid (2 ml) were added to the reaction mixture, which was stirred at room temperature for 12 hours. The reaction mixture was made basic by adding 1N aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried and concentrated. The residue was purified by alumina column chromatography (eluent: ethyl acetate/hexane=1/50). A methanol solution (3 ml) of oxalic acid dehydrate (149 mg) was added to a methanol solution (10 ml) of the residue, which was concentrated. Ethyl acetate was added to the residue, and the precipitates were collected by filtration to give the entitled compound (3.130 g) as an amorphous powder.

Provenance & Evidence