Reaction #1328414

Reaction equation

(R)-7-Diethylaminocarbonylmethyloxy-3-(2-phthalimidopropyl)indole

hydrazine monohydrate

→

title compound

Yield 96.0%

(R)-7-diethylaminocarbonylmethyloxy-3-(2-aminopropyl)indole

Yield 96.0%

Solvents

ethanol

Conditions

Workup

1. 1
   TemperatureThe suspension was heated
2. 2
   TemperatureAfter cooling down
3. 3
   Filtrationwere filtered off
4. 4
   Concentrationthe filtrate was concentrated under reduced pressure
5. 5
   workup.ADDITIONEthyl acetate and a sodium hydroxide aqueous solution were added to the residue
6. 6
   Washthe organic layer was further washed with a sodium hydroxide aqueous solution
7. 7
   Otherdried
8. 8
   OtherThe solution was evaporated under reduced pressure
9. 9
   OtherThe resulting residue was slowly crystallized
10. 10
    Otherdried under reduced pressure

Procedure

(R)-7-Diethylaminocarbonylmethyloxy-3-(2-phthalimidopropyl)indole 10.27 g was suspended in 100 ml of ethanol, and 2.5 ml of hydrazine monohydrate was added thereto. The suspension was heated to reflux in an oil bath of 85° C. For 3 hours. After cooling down, the resulting deposited insoluble materials were filtered off, and the filtrate was concentrated under reduced pressure. Ethyl acetate and a sodium hydroxide aqueous solution were added to the residue and distributed in liquid-liquid, and the organic layer was further washed with a sodium hydroxide aqueous solution and dried. The solution was evaporated under reduced pressure. The resulting residue was slowly crystallized, and dried under reduced pressure, whereby 6.90 g of the title compound was obtained in the form of a pale brownish white substance.

Source