((Chloromethyl)sulphonyl)benzene → 1-Benzyl-4-{4-nitro-3-[(phenylsulfonyl)methyl]phenyl}piperazine

HRID 227293

反応式

HRID 227293 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:24][S:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:27])=[O:26].O(C(C)(C)C)[K]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[C:18]([CH2:24][S:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)(=[O:27])=[O:26])[CH:19]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 81625((Chloromethyl)sulphonyl)benzeneHCID 27474271-Benzyl-4-(4-nitrophenyl)piperazineHCID 178418922HCID 178418922、化合物

生成物 1

HCID 442428861-Benzyl-4-{4-nitro-3-[(phenylsulfonyl)methyl]phenyl}piperazine収率 83%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-20 °C

実験手順

A stirred solution of 1-benzyl-4-(4-nitrophenyl)piperazine (5.95 g, 20.0 mmol) and chloromethylphenylsulfone (3.82 g, 20.0 mmol) in dry THF under nitrogen at −60° C. is treated with 1.0M KO-t-Bu in THF (44.0 mL, 44.0 mmol), warmed to −20° C. over a 1 h period, quenched with acetic acid and treated sequentially with water, saturated aqueous NaHCO3 and ether. The phases are separated and the aqueous phase is extracted with ether. The combined ethers are washed with water and brine, dried over MgSO4 and concentrated in vacuo. The resultant residue is chromatographed (silica gel, 1:1 and 1:0 ethyl acetate:hexanes as eluent) to give the title compound as a yellow solid, 7.52 g (83% yield), mp 145-146° C., characterized by NMR and mass spectral analyses.

後処理

  1. customquenched with acetic acid
  2. additiontreated sequentially with water, saturated aqueous NaHCO3 and ether
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted with ether
  5. washThe combined ethers are washed with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue is chromatographed (silica gel, 1:1 and 1:0 ethyl acetate:hexanes as eluent)

出典と根拠

ORDレコード
ord-a74a25ab7e974c9e9b47fde5425c2c4f
出典データセット
uspto-grants-2009_07
特許番号
US07560470B2

関連ノート

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