Reacción #54486

ord-2ea726274d5b438283d3b7d1fe3bc327

Ecuación de reacción

Cl.Cl.Nc1c(F)c(N)c(F)c(F)c1F
dihydrochloride
CN1CCN(C(=O)c2c(N3CCNCC3)n(-c3ccccc3)c3ccccc23)CC1
1-phenyl-2-(1-piperazinyl)-indole 3-carboxylic acid (4-methyl)-piperazide
ClCCC1OCCO1
2-(2-chloroethyl)-1,3-dioxolane
CCN(CC)CC
triethylamine
CN1CCN(C(=O)c2c(N3CCN(CCC4OCCO4)CC3)n(-c3ccccc3)c3ccccc23)CC1
2-[4-(2-(1,3-dioxolan-2-yl)-ethyl)-1-piperazinyl]-1-phenyl indole 3-carboxylic acid (4-methyl)-piperazide

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturawas maintained at the boil for 40 hours
  2. 2
    TemperaturaAfter cooling
  3. 3
    Lavadowashed three times with water
  4. 4
    OtroThe resinous residue of the organic phase was chromatographed
  5. 5
    LavadoThe base was eluted as a resin
  6. 6
    Otrotheoretical yield)

Procedimiento

A stirred mixture of 8 g (0.02 mol) of 1-phenyl-2-(1-piperazinyl)-indole 3-carboxylic acid (4-methyl)-piperazide, 9.45 g (0.07 mol) of 2-(2-chloroethyl)-1,3-dioxolane and 9.7 ml of triethylamine in 60 ml of toluene was maintained at the boil for 40 hours. After cooling, the mixture was diluted with 200 ml of chloroform, washed three times with water, and the solvent was eliminated in vacuo. The resinous residue of the organic phase was chromatographed using silica gel 60 (0.06-0.2 mm, deactivated by 10% of water, column size: 3 × 100 cm) with chloroform containing 10% methanol. The base was eluted as a resin. The yield amounted to 6.6 g (66% of the theoretical yield). The dihydrochloride melted at 215°-217° C.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04148895uspto-grants-1979_04