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

HRID 1795323노트

반응식

HRID 1795323 반응식
[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]

참가 물질

5

반응물 2

HCID 222AmmoniaHCID 2834838ST088463

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d2e29cf5e44d423fb43e16e2c342e894
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07026314B2

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