Toluene → 4-Benzyloxycarbonyl-1-[4-(4-pyridyl)benzyl]-2-piperazinone

HRID 1840535노트

반응식

HRID 1840535 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][C:21](Br)=[CH:20][CH:19]=2)[C:13](=[O:25])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:26]1[CH:31]=[CH:30][C:29](OB(O)O)=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>C(OCC)(=O)C.C(O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:29]3[CH:30]=[CH:31][N:26]=[CH:27][CH:28]=3)=[CH:20][CH:19]=2)[C:13](=[O:25])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 218058124-Pyridylboric acidHCID 23447549Benzyl 4-[(4-bromophenyl)methyl]-3-oxopiperazine-1-carboxylate

생성물 1

HCID 234475764-Benzyloxycarbonyl-1-[4-(4-pyridyl)benzyl]-2-piperazinone수율 40.1%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 4-benzyloxycarbonyl-1-(4-bromobenzyl)-2-piperazinone (807 mg), 4-pyridylboric acid (244 mg), tetrakis (triphenylphosphine)palladium (69 mg), 2M sodium carbonate solution (2 ml), toluene (8 ml) and ethanol (2 ml) was refluxed overnight. After the mixture was cooled, ethyl acetate was added to the reaction solution. The mixture was washed with water and saturated brine, dried (MgSO4) and concentrated. The residue was purified with silica gel column chromatography (ethyl acetate) to give colorless crystals of the title compound (283 mg).

후처리

  1. temperaturewas refluxed overnight
  2. temperatureAfter the mixture was cooled
  3. washThe mixture was washed with water and saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel column chromatography (ethyl acetate)

출처 및 근거

ORD 기록
ord-6045df75ebf54ba3b4ee5e4747db18f6
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06680312B2

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