Water → 5-Amino-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indole

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Reaction Steps

A portion (2.3 g) of the compound obtained in Example 41 was dissolved in a mixed solvent of methylene chloride (450 ml) and methanol (450 ml) and to the solution were added ammonium acetate (7.12 g) and sodium cyanoborohydride (0.76 g). The mixture was stirred for 3 days at room temperature. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate-ethyl acetate/methanol=9:1) to yield 1.2 g (52%) of the titled compound as pale brown crystals.

Provenance & Evidence