Ammonia → 4-(4-Methanesulfonyl-piperazin-1-yl)-phenylamine

HRID 1795323ノート

反応式

HRID 1795323 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([S:16]([CH3:19])(=[O:18])=[O:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.N>CO.[Pd]>[CH3:19][S:16]([N:13]1[CH2:12][CH2:11][N:10]([C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH2:15][CH2:14]1)(=[O:17])=[O:18]

参加物

5

反応物 2

HCID 222AmmoniaHCID 2834838ST088463

生成物 1

HCID 9419144-(4-Methanesulfonyl-piperazin-1-yl)-phenylamine収率 27.5%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒2 回

実験手順

4-(4-Nitrophenyl)-1-methylsulfonylpiperazine (3.83 g, 13.4 mmol), as prepared in Reference Example 12a above, was mixed in methanol (100 ml) and 2 M ammonia in methanol (50 ml) and 10% palladium on carbon (400 mg) was added. The mixture was hydrogenated on a Paar apparatus (50 psi) for 3 h. The reaction was allowed to cool, the catalyst was filtered, washed with methanol then washed with chloroform. The chloroform portion contained a minor amount of the desired but looked purer. The chloroform portion was concentrated in vacuo and was recrystallized ethyl acetate to give 4-[4-(methylsulfonyl)-1-piperazinyl]benzenamine as a shiny brown solid (0.94 g, 27% yield, mp 192–193° C.). GC/MS (EI, M+) m/z=255.

後処理

  1. temperatureto cool
  2. filtrationthe catalyst was filtered
  3. washwashed with methanol
  4. washthen washed with chloroform
  5. concentrationThe chloroform portion was concentrated in vacuo
  6. customwas recrystallized ethyl acetate

出典と根拠

ORDレコード
ord-d2e29cf5e44d423fb43e16e2c342e894
出典データセット
uspto-grants-2006_04
特許番号
US07026314B2

反応ノート

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