Sodium amide → 5,6,7,8-Tetrahydroisoquinolin-1-amine

Participants

Reaction Conditions

Reaction Steps

Using the method described in Example 63, Step B, a mixture of 2.0 g (15.0 mmol) of 5,6,7,8-tetrahydroisoquinoline and 644 mg (16.5 mmol) of sodium amide in 2.5 mL of xylene was stirred at 150° C. overnight. The crude material was purified by flash column chromatography on silica gel eluting with 0-100% ethyl acetate/dichloromethane, and the partially purified material was distilled using a Kugelrohr apparatus at 100-105° C. (0.3 mm). Recrystallization of the distallate from a hexane/toluene mixture gave 120 mg of 1-amino-5,6,7,8-tetrahydroisoquinoline as a white solid containing approximately 7% of 1-aminoisoquinoline.

Provenance & Evidence