Reacción #44400

ord-258c082de91b464ba0230efdebd317cf

Ecuación de reacción

Cl
hydrochloride
Cl.Cl.Cl.N[C@H]1CC[C@H](CCN2CCN(c3cccc(Cl)c3Cl)CC2)CC1
trans-4-{2-[4-(2,3-dichlorophenyl)-piperazin-1-yl]-ethyl}-cyclohexyl-amine trihydrochloride
CCN(CC)CC
triethylamine
O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl
triphosgene
CCN(CC)CC
triethylamine
CN(C)C(=O)N[C@H]1CC[C@H](CCN2CCN(c3cccc(Cl)c3Cl)CC2)CC1
title compound
Rendimiento 143.6%
CN(C)C(=O)N[C@H]1CC[C@H](CCN2CCN(c3cccc(Cl)c3Cl)CC2)CC1
Trans-1-{4-[2-[4-(2,3-dichlorophenyl)-piperazin-1-yl]-ethyl]-cyclohexyl}-3,3-dimethyl-urea
Rendimiento 143.6%

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.ADDITIONwas dropped in
  2. 2
    workup.ADDITIONwas added
  3. 3
    FiltraciónThe mixture was filtered
  4. 4
    Lavadothe filtrate washed with water
  5. 5
    Otrodried
  6. 6
    Otroevaporated in vacuo
  7. 7
    OtroRecrystallizing the product from methanol

Procedimiento

0.56 g (1.2 mmol) trans-4-{2-[4-(2,3-dichlorophenyl)-piperazin-1-yl]-ethyl}-cyclohexyl-amine trihydrochloride was suspended in dry dichloromethane (50 ml), triethylamine 0.77 ml, 6 mmol) was added and 0.13 g (0.44 mmol) triphosgene dissolved in dichloromethane was dropped in. After one hour stirring at room temperature dimetilamine hydrochloride (0.49 g, 6 mmol) followed by triethylamine (0.84 ml, 6 mmol) was added and the stirring was continued for 20 hours. The mixture was filtered, the filtrate washed with water, dried and evaporated in vacuo. Recrystallizing the product from methanol gave the title compound (0.27 g, 52%). Melting point: 212-4° C.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07737142B2uspto-grants-2010_06