Reacción #595414

ord-c6e0f4394fac4981baacb36d8a198c26

Ecuación de reacción

OC(CCl)CNc1ccccc1
product
OC(CCl)CNc1ccccc1
1-chloro-3-(phenylamino)propan-2-ol
[K+].[OH-]
KOH
c1ccc(NCC2CO2)cc1
colorless oil
Rendimiento 95.0%
c1ccc(NCC2CO2)cc1
N-(oxiran-2-ylmethyl)aniline
Rendimiento 95.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Lavadowashed with 1M HCl and brine
  2. 2
    SecadoThe organic layer was dried with MgSO4
  3. 3
    Concentraciónconcentrated
  4. 4
    Otroto give crude product
  5. 5
    OtroIt was further purified by silica gel chromatography

Procedimiento

To a solution of the product of Step 3 (185.7 mg, 1.0 mmol, 1 equiv) in 1,4-dioxane (3.3 mL) was added KOH powder (67.3 mg, 1.2 mmol, 1.2 equiv). The mixture was stirred at room temperature for 24 hours. The mixture was diluted with EtOAc and washed with 1M HCl and brine. The organic layer was dried with MgSO4 and concentrated to give crude product. It was further purified by silica gel chromatography using 20% EtOAc/Hex to afford 141.8 mg colorless oil as product, yield 95.0%.

Fuente

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