Piperazine → 1-(4-(Methylsulfonyl)phenyl)piperazine

HRID 509267ノート

反応式

HRID 509267 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CO.O>[CH3:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:3][CH:4]=1)(=[O:10])=[O:9]

参加物

9

反応物 4

HCID 4837PiperazineHCID 770141-Bromo-4-(methylsulphonyl)benzeneHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxide

生成物 1

HCID 7359041-(4-(Methylsulfonyl)phenyl)piperazine収率 20%

試薬・触媒・溶媒 4

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

1-Bromo-4-(methylsulfonyl)benzene (275 mg, 1.169 mmol), piperazine (302 mg, 3.507 mmol), Pd2(dba)3 (21 mg, 0.023 mmol), BINAP (44 mg, 0.070 mmol), and sodium-tert-butoxide (169 mg, 1.754 mmol) were suspended in toluene (5 ml), and then the resulting liquid was stirred at 100° C. under nitrogen stream for 15 hours. Distilled water (15 ml) was added to the resulting reaction liquid, followed by extraction with MC (20 ml×3). The organic layer was dried over anhydrous sodium sulfate, followed by filtration and concentration, and then the residue thus obtained was subjected to MPLC (15% MeOH/MC), to obtain 56 mg of pale yellow solid (20%).

後処理

  1. extractionfollowed by extraction with MC (20 ml×3)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfollowed by filtration and concentration
  4. customthe residue thus obtained

出典と根拠

ORDレコード
ord-a98802b486a64799b16b62726b1c72ee
出典データセット
uspto-grants-2015_08
特許番号
US09096571B2

反応ノート

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