Formic Acid → 5-(N-methylamino)-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indole

A portion (100 mg) of the compound obtained in Example 81 was suspended in tetrahydrofuran (THF; 3 ml) and to the suspension was added a solution (1M; 0.5 ml) of an acid anhydride prepared from acetic anhydride and formic acid in THF at -20° C. The mixture was stirred for 20 minutes. The solid obtained by concentrating the reaction mixture was suspended in THF (3 ml) and to the suspension was added a solution of borane-methyl sulfide complex in THF (10M; 100 μl). The mixture was heated to reflux for 1 hour and allowed to cool. 3N solution (10 ml) of hydrochloric acid in methanol was added to the reaction mixture, followed by stirring for 1 hour at room temperature. The reaction mixture was made basic with 3N aqueous solution of sodium hydroxide and extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure to yield 90 mg (85%) of the titled compound.

1. customThe solid obtained
2. concentrationby concentrating the reaction mixture
3. additionwas added a solution of borane-methyl sulfide complex in THF (10M; 100 μl)
4. temperatureThe mixture was heated
5. temperatureto reflux for 1 hour
6. temperatureto cool
7. addition3N solution (10 ml) of hydrochloric acid in methanol was added to the reaction mixture
8. stirringby stirring for 1 hour at room temperature
9. extractionextracted with ethyl acetate
10. washThe organic layer was washed with saturated aqueous solution of sodium chloride
11. dry with materialdried over anhydrous sodium sulfate
12. distillationThen, the solvent was distilled off under reduced pressure

ORD record

ord-e7750f95b71446839892c23e4f9ab82b

Source dataset

uspto-grants-2000_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06040331