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

HRID 1052304ノート

反応式

HRID 1052304 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)触媒HCID 1140Toluene溶媒

反応条件

温度
105 °C

実験手順

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.

後処理

  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%)

出典と根拠

ORDレコード
ord-37c336a856ac4539bbac69e60a34e007
出典データセット
uspto-grants-2016_07
特許番号
US09388185B2

反応ノート

読み込み中…