تفاعل #969142

معادلة التفاعل

N-trifluoroacetyl-2-iodo-4-chlorophenethylamine

KOAc

PPh3

→

clear oil

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

المذيبات

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe product mixture was cooled to 20 C
2. 2
   ترشيحfiltered
3. 3
   workup.ADDITIONdiluted with water (100 mL)
4. 4
   استخلاصextracted with ether (3×100 mL)
5. 5
   غسيلthe combined organic phases washed with water (100 mL), brine (100 mL)
6. 6
   تجفيفdried with Na2SO4
7. 7
   تركيزconcentrated

الإجراء التجريبي

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.

المصدر