1,4-Dibromobenzene → 4-(4-Bromophenyl)-1-methyl-2-piperazinone

HRID 1052304노트

반응식

HRID 1052304 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.Cl.[CH3:10][N:11]1[CH2:16][CH2:15][NH:14][CH2:13][C:12]1=[O:17].C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([N:14]2[CH2:15][CH2:16][N:11]([CH3:10])[C:12](=[O:17])[CH2:13]2)=[CH:3][CH:4]=1

참가 물질

7

반응물 3

HCID 78041,4-DibromobenzeneHCID 10796Cesium carbonateHCID 170607661-Methylpiperazin-2-one--hydrogen chloride (1/1)

생성물 1

HCID 899635354-(4-Bromophenyl)-1-methyl-2-piperazinone수율 96.6%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)촉매HCID 1140Toluene용매

반응 조건

온도
105 °C

실험 절차

A mixture of 1,4-dibromobenzene (470 mg, 2.0 mmol), 1-methylpiperazin-2-one hydrochloride (150 mg, 1.0 mmol, from J&W PharmLab), palladium acetate (6.7 mg, 0.030 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.035 g, 0.060 mmol), and cesium carbonate (0.98 g, 3.0 mmol) in toluene (5.0 mL) was evacuated and refilled with nitrogen three times and then the reaction was stirred at 105° C. overnight. The mixture was diluted with ethyl acetate, washed with water, brine, then dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexane (0-60%) to afford the desired product (0.26 g, 49%). LCMS calculated for C11H14BrN2O (M+H)+: m/z=269.0. Found 269.0.

후처리

  1. customwas evacuated
  2. additionrefilled with nitrogen three times
  3. additionThe mixture was diluted with ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexane (0-60%)

출처 및 근거

ORD 기록
ord-37c336a856ac4539bbac69e60a34e007
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388185B2

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