Acetonitrile → 2-Acetyl-3-(N,N-dimethylaminomethyl)-indole

HRID 467240

반응식

HRID 467240 반응식
[Cl-].C[CH:3]=[N+:4]=[CH:5]C.[C:7]([C:10]1[NH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:9])[CH3:8].[C:19](#N)C>>[C:7]([C:10]1[NH:11][C:12]2[C:17]([C:18]=1[CH2:3][N:4]([CH3:5])[CH3:19])=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:9])[CH3:8]

참가 물질

4

반응물 3

HCID 6342AcetonitrileHCID 5890812-AcetylindoleHCID 21873455N,N-dimethylmethylene ammonium chloride

생성물 1

HCID 144595432-Acetyl-3-(N,N-dimethylaminomethyl)-indole

실험 절차

187 g (2 mols) N,N-dimethylmethyleneammonium chloride are suspended under an inert gas (nitrogen or argon) in 28 liters anhydrous acetonitrile. The stirred suspension is mixed with 159 g (1 mol) pulverized and dried 2-acetylindole, heated to the boil and, while stirring continuously, uniformly cooled over the course of 7 hours to 25° C. It is stirred overnight at 20°-25° C. The acetonitrile is substantially distilled off under vacuum and the remaining residue taken up in 20 liters of water and adjusted to pH 9-10 with concentrated ammonium hydroxide solution. This solution is stirred up three times with, in each case, 5 liters of dichloromethane. The organic phases are combined and washed with 5 liters of water. The organic phase is dried by the addition of anhydrous sodium sulphate, filtered and mixed with 5 liters tert-butyl methyl ether. The dichloromethane is substantially distilled off, the crystallization of the product thereby already commencing. This is completed by leaving to stand overnight at +4° C. The product is filtered off with suction, washed with n-hexane and dried under a vacuum. Yield: 141.7 g (65.6% of theory).

후처리

  1. additionThe stirred suspension is mixed with 159 g (1 mol)
  2. temperatureuniformly cooled over the course of 7 hours to 25° C
  3. stirringIt is stirred overnight at 20°-25° C
  4. distillationThe acetonitrile is substantially distilled off under vacuum
  5. stirringThis solution is stirred up three times with, in each case, 5 liters of dichloromethane
  6. washwashed with 5 liters of water
  7. dry with materialThe organic phase is dried by the addition of anhydrous sodium sulphate
  8. filtrationfiltered
  9. additionmixed with 5 liters tert-butyl methyl ether
  10. distillationThe dichloromethane is substantially distilled off
  11. customthe crystallization of the product
  12. customby leaving
  13. filtrationThe product is filtered off with suction
  14. washwashed with n-hexane
  15. customdried under a vacuum

출처 및 근거

ORD 기록
ord-6d2e7e4d402f42a9948b2c6915cd1b24
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05159080

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