Hydrochloric Acid → 7-Phenyl-1,2,3,4-tetrahydroisoquinoline

To a solution of 7-phenylisoquinoline (1.25 g, 6.1 mmol)in methanol (50 ml) was added conc HCl (2 ml) and platinum oxide (100 mg). The reaction mixture was hydrogenated at 50 psi until no further uptake of hydrogen was observed. The catalyst was filtered off, washed with methanol. The filtrate was evaporated under reduced pressure to give a solid. The solid was partitioned between ethyl acetate and sodium carbonate solution. The aqueous solution was extracted with ethyl acetate (2×100 ml). The ethyl acetate extracts were combined, washed with brine (2×100 ml), dried over magnesium sulphate, filtered and evaporated under reduced pressure to give an oil, which crystallised on standing. The solid was a mixture of the title compound and 7-phenyl-decahydroisoquinoline; Rf 0.66 (EtOAc/MeOH/NH3 5:1:1).

1. filtrationThe catalyst was filtered off
2. washwashed with methanol
3. customThe filtrate was evaporated under reduced pressure
4. customto give a solid
5. customThe solid was partitioned between ethyl acetate and sodium carbonate solution
6. extractionThe aqueous solution was extracted with ethyl acetate (2×100 ml)
7. washwashed with brine (2×100 ml)
8. dry with materialdried over magnesium sulphate
9. filtrationfiltered
10. customevaporated under reduced pressure
11. customto give an oil, which
12. customcrystallised
13. additiona mixture of the title compound and 7-phenyl-decahydroisoquinoline

ORDレコード

ord-6640fbad419d4305812f55b35ca94910

出典データセット

uspto-grants-1997_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05700809