Acetic Acid → 4-Benzyloxycarbonyl-1-[1-(4-pyridyl)-4-piperidinylamino]-2-piperazinone

HRID 2086234노트

반응식

HRID 2086234 반응식
[NH2:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][C:3]1=[O:18].[N:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][C:28](=O)[CH2:27][CH2:26]2)=[CH:21][CH:20]=1.C(O)(=O)C.[Na]>C(O)C.CO>[CH2:11]([O:10][C:8]([N:5]1[CH2:6][CH2:7][N:2]([NH:1][CH:28]2[CH2:27][CH2:26][N:25]([C:22]3[CH:23]=[CH:24][N:19]=[CH:20][CH:21]=3)[CH2:30][CH2:29]2)[C:3](=[O:18])[CH2:4]1)=[O:9])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 5360545SodiumHCID 113327931-(Pyridin-4-yl)piperidin-4-oneHCID 22727156Benzyl 4-amino-3-oxopiperazine-1-carboxylate

생성물 1

HCID 178254544-Benzyloxycarbonyl-1-[1-(4-pyridyl)-4-piperidinylamino]-2-piperazinone수율 70.2%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 887Methanol용매

반응 조건

온도
0 °C

실험 절차

A solution of 1-amino-4-benzyloxycarbonyl-2-piperazinone (21.92 g) and 1-(4-pyridyl)-4-piperidone (15.51 g) in ethanol (500 ml) was dehydrated using a Soxlet extractor packed with molecular sieves 4A while refluxing for 24 hours. The reaction mixture was concentrated to obtain a residue, which was dissolved in methanol (300 ml) and combined with acetic acid (18.26 g) with cooling on ice followed by sodium cycanoborohydride (7.16 g) and then stirred at 0° C. for 3 hours. The reaction mixture was concentrated, and the residue was combined with a 1N aqueous solution of sodium hydroxide, and extracted with methylene chloride. The extract was washed with water and brine, dried and concentrated to obtain 4-benzyloxycarbonyl-1-[1-(4-pyridyl)-4-piperidinylamino]-2-piperazinone (25.29 g) as a pale yellow amorphous material.

후처리

  1. temperaturewhile refluxing for 24 hours
  2. concentrationThe reaction mixture was concentrated
  3. customto obtain a residue, which
  4. temperaturewith cooling on ice
  5. concentrationThe reaction mixture was concentrated
  6. extractionextracted with methylene chloride
  7. washThe extract was washed with water and brine
  8. customdried
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-75179fc5facb4f8ea50aa3e0bad61c1a
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06723722B1

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