Reacción #595396

ord-028016107ac5438fb8dc40d6d7facb0b

Ecuación de reacción

Cc1ccc(NN)cc1.Cl
p-tolylhydrazine hydrochloride
CCOC(=O)N1CCC(=O)CC1
1-carbethoxy-4-piperidone
CCOC(=O)N1CCc2[nH]c3ccc(C)cc3c2C1
desired product
Rendimiento 86.0%
CCOC(=O)N1CCc2[nH]c3ccc(C)cc3c2C1
Ethyl 8-Methyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate
Rendimiento 86.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturaheated
  2. 2
    Temperaturato reflux for 2 hours
  3. 3
    OtroThe reaction mixture was removed
  4. 4
    Temperaturafrom heat
  5. 5
    FiltraciónThe resulting mixture was filtered
  6. 6
    Lavadowashed with 50% aqueous EtOH

Procedimiento

Following a literature procedure (Harbert et al., J. Med. Chem. 1980, 23, 635-643) p-tolylhydrazine hydrochloride (0.500 g, 3.15 mmol) and 1-carbethoxy-4-piperidone (0.18 mL, 1.17 mmol) were suspended in EtOH (0.880 mL) and heated to reflux for 2 hours. The reaction mixture was removed from heat and allowed to stand overnight at ambient temperature. The resulting mixture was filtered and washed with 50% aqueous EtOH to afford the desired product as a beige powder (259 mg, 86%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09095572B2uspto-grants-2015_08