Reacción #969142

Ecuación de reacción

N-trifluoroacetyl-2-iodo-4-chlorophenethylamine

KOAc

PPh3

→

clear oil

N-Trifluoroacetyl-8-chloro-1-methylene-2,3,4,5-tetrahydro-1H-3-benzazepine

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe product mixture was cooled to 20 C
2. 2
   Filtraciónfiltered
3. 3
   workup.ADDITIONdiluted with water (100 mL)
4. 4
   Extracciónextracted with ether (3×100 mL)
5. 5
   Lavadothe combined organic phases washed with water (100 mL), brine (100 mL)
6. 6
   Secadodried with Na2SO4
7. 7
   Concentraciónconcentrated

Procedimiento

A solution of N-allyl, N-trifluoroacetyl-2-iodo-4-chlorophenethylamine (0.76 g, 1.8 mmol) in dimethylformamide (20 mL) was treated with KOAc (0.53 g, 5.4 mmol), n-Bu4NBr (0.58 g, 1.8 mmol), PPh3 (0.047 g, 0.18 mmol), Pd(OAc)2 (0.041 g, 0.18 mmol) and stirred overnight at 105 C. The product mixture was cooled to 20 C, filtered, diluted with water (100 mL), extracted with ether (3×100 mL), the combined organic phases washed with water (100 mL), brine (100 mL), dried with Na2SO4 and concentrated. Flash chromatography (10% EtOAc in hexane, silica) resulted in 0.228 g of a clear oil. 1H NMR (400 MHz, CDCl3) d 7.29 (s, 1H), 7.18 (m, 1H), 7.04 (m, 1H), 5.38 (m, 2H), 5.40 (d, J=16 Hz, 2H), 3.80 (m, 2H), 3.00 (m, 2H). MS calculated for C13H11ClF3NO+H: 290, observed: 290.

Fuente