Triphenylphosphine → 4-(2-chloroethyl)-1-methyl-4,5,6,7-tetrahydro-1H-indole

HRID 447748노트

반응식

HRID 447748 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][N:21]1[C:29]2[CH2:28][CH2:27][CH2:26][CH:25]([CH2:30][CH2:31]O)[C:24]=2[CH:23]=[CH:22]1.C(Cl)(Cl)(Cl)[Cl:34].C(#N)C>>[Cl:34][CH2:31][CH2:30][CH:25]1[CH2:26][CH2:27][CH2:28][C:29]2[N:21]([CH3:20])[CH:22]=[CH:23][C:24]1=2

참가 물질

4

반응물 3

HCID 11776TriphenylphosphineHCID 18669661Acetonitrile tetrachloromethaneHCID 578144052-(1-methyl-4,5,6,7-tetrahydro-1H-indol-4-yl)ethanol

생성물 1

HCID 690791294-(2-chloroethyl)-1-methyl-4,5,6,7-tetrahydro-1H-indole수율 43%

실험 절차

Triphenylphosphine (2.46 g, 9.38 mmol) is added to a solution of 2-(1-methyl-4,5,6,7-tetrahydro-1H-indol-4-yl)ethanol (1.68 g, 9.38 mmol) in CCl4/Acetonitrile 1:1 (20 mL) at room temperature and the mixture is maintained under stirring for 3 hours monitoring the reaction by TLC. The solution is concentrated to half the volume at reduced pressure, CH2Cl2 is added and washed with water. The organic phase is separated and evaporated to dryness. The crude is treated with diethyl ether and the precipitated is filtered. The diethyl ether is evaporated at reduced pressure, and the resulting crude is purified by column chromatography, giving 4-(2-chloroethyl)-1-methyl-4,5,6,7-tetrahydro-1H-indole (0.8 g, 4.05 mmol, 43%, oil). (ESI-MS m/z 198 (M+H)+.

후처리

  1. temperaturethe mixture is maintained
  2. customthe reaction by TLC
  3. concentrationThe solution is concentrated to half the volume at reduced pressure, CH2Cl2
  4. additionis added
  5. washwashed with water
  6. customThe organic phase is separated
  7. customevaporated to dryness
  8. additionThe crude is treated with diethyl ether
  9. filtrationthe precipitated is filtered
  10. customThe diethyl ether is evaporated at reduced pressure
  11. customthe resulting crude is purified by column chromatography

출처 및 근거

ORD 기록
ord-f354015d5b914b869b6f71e3104e19bd
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481567B2

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