Reaktion #63509

Reaktionsgleichung

1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline

2-nitrophenylacetic acid

→

N-(2-nitrophenylacetyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline

Ausbeute 72.1%

Reaktionsbedingungen

Vorschrift

Using the procedures described in Example 3 hereinabove, 9.4 g of 1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline is reacted with 8.0 g 2-nitrophenylacetic acid to give 11.8 g N-(2-nitrophenylacetyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline. This amide is reduced with borane in THF to produce 13.2 g of N-(2-nitrophenethyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline hydrochloride. Reduction of the nitro function by catalytic hydrogenation over palladium provides, after recrystallization from ethanol/ether and drying under vacuum, 9.6 g N-(2-aminophenethyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline dihydrochloride, m.p. 229°-230°.

Quelle