3-Bromopropionitrile → 4-[alpha-(2-Pyridyl)benzyl]-1-(2-cyanoethyl)piperazine

HRID 129759

반응식

HRID 129759 반응식
C(N(C(C)C)CC)(C)C.[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH:16]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Br[CH2:30][CH2:31][C:32]#[N:33]>C(Cl)Cl>[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH:16]([N:23]1[CH2:28][CH2:27][N:26]([CH2:30][CH2:31][C:32]#[N:33])[CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

5

반응물 3

HCID 170203-BromopropionitrileHCID 81531DiisopropylethylamineHCID 33464461-[Phenyl(pyridin-2-yl)methyl]piperazine

생성물 1

HCID 193703624-[alpha-(2-Pyridyl)benzyl]-1-(2-cyanoethyl)piperazine수율 88%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

1.05 g of N,N-diisopropyl-N-ethylamine was added, with stirring, to a solution of 2.0 g of 4-[α-(2-pyridyl)benzyl]piperazine and 1.0 g of 3-bromopropionitrile in 20 ml of methylene chloride, whilst ice-cooling, and the mixture was stirred at room temperature for 16 hours. At the end of this time, the mixture was poured into ice-water and extracted with chloroform. The extracts were combined and dried over anhydrous sodium sulfate, after which the solvent as removed by evaporation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 20:1 by volume mixture of ethyl acetate and ethanol as the eluent, to give 2:1 g (yield 88%) of the title compound as crystals, melting at 114°-116° C.

후처리

  1. temperaturecooling
  2. extractionextracted with chloroform
  3. dry with materialdried over anhydrous sodium sulfate
  4. customafter which the solvent as removed by evaporation under reduced pressure
  5. customThe resulting residue was purified by column chromatography through silica gel
  6. additionby volume mixture of ethyl acetate and ethanol as the eluent
  7. customto give 2

출처 및 근거

ORD 기록
ord-eb8b5e04c7ed4533942187c2f4999c2b
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05470851

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