Reacción #1328414

ord-aa7188ec5e114b029020b4845f5c56a1

Ecuación de reacción

CCN(CC)C(=O)COc1cccc2c(C[C@@H](C)N3C(=O)c4ccccc4C3=O)c[nH]c12
(R)-7-Diethylaminocarbonylmethyloxy-3-(2-phthalimidopropyl)indole
NN.O
hydrazine monohydrate
CCN(CC)C(=O)COc1cccc2c(C[C@@H](C)N)c[nH]c12
title compound
Rendimiento 96.0%
CCN(CC)C(=O)COc1cccc2c(C[C@@H](C)N)c[nH]c12
(R)-7-diethylaminocarbonylmethyloxy-3-(2-aminopropyl)indole
Rendimiento 96.0%

Disolventes

Condiciones de reacción

Temperatura
85°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaThe suspension was heated
  2. 2
    TemperaturaAfter cooling down
  3. 3
    Filtraciónwere filtered off
  4. 4
    Concentraciónthe filtrate was concentrated under reduced pressure
  5. 5
    workup.ADDITIONEthyl acetate and a sodium hydroxide aqueous solution were added to the residue
  6. 6
    Lavadothe organic layer was further washed with a sodium hydroxide aqueous solution
  7. 7
    Otrodried
  8. 8
    OtroThe solution was evaporated under reduced pressure
  9. 9
    OtroThe resulting residue was slowly crystallized
  10. 10
    Otrodried under reduced pressure

Procedimiento

(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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07115412B2uspto-grants-2006_10