1-Butanol → 1-(N-benzyloxycarbonyl-p-toluidinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

N-benzyloxycarbonyl-p-toluidinoacetaldehyde diethyl acetal (6 g) and 3,4-dihydroxyphenethylamine hydrochloride (2.5 g) were added to a mixture of n-butyl alcohol (60 ml) and water (8.5 ml) and then the mixture was refluxed for 9.5 hours in a stream of nitrogen. In the course of the reaction, the above-mentioned acetal (0.6 g) was twice added to the mixture, after 5 hours and after 7.5 hours from the beginning of the reaction. The reaction mixture was concentrated and the residue was washed with ether and dissolved in hot water (300 ml). After the insoluble material was filtered off, the filtrate was washed with ethyl acetate and treated with activated charcoal. The aqueous layer was concentrated to dryness to give amorphous 1-(N-benzyloxycarbonyl-p-toluidinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (3.8 g), mp 125° C. (dec).

1. temperaturethe mixture was refluxed for 9.5 hours in a stream of nitrogen
2. customIn the course of the reaction
3. concentrationThe reaction mixture was concentrated
4. washthe residue was washed with ether
5. dissolutiondissolved in hot water (300 ml)
6. filtrationAfter the insoluble material was filtered off
7. washthe filtrate was washed with ethyl acetate
8. additiontreated with activated charcoal
9. concentrationThe aqueous layer was concentrated to dryness

ORD record

ord-450ae31ddfe24a7bb4c2f7e67aba0817

Source dataset

uspto-grants-1980_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04220647