Ammonium formate → 5-Methyl-4-(4-methylpiperazin-1-yl)-2-(propan-2-yloxy)aniline

HRID 518825노트

반응식

HRID 518825 반응식
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[C:12]([O:14][CH:15]([CH3:17])[CH3:16])[C:11]([N+:18]([O-])=O)=[CH:10][C:9]=2[CH3:21])[CH2:4][CH2:3]1.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:21][C:9]1[C:8]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[CH:13][C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[C:11]([CH:10]=1)[NH2:18]

참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 866979901-Methyl-4-[2-methyl-4-nitro-5-(propan-2-yloxy)phenyl]piperazine

생성물 1

HCID 866979915-Methyl-4-(4-methylpiperazin-1-yl)-2-(propan-2-yloxy)aniline수율 191%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

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온도
80 °C

실험 절차

Two 20 ml tubes each containing a mixture of 614 mg of 1-methyl-4-[2-methyl-4-nitro-5-(propan-2-yloxy)phenyl]piperazine, 185 mg of 10% Pd on carbon and 793 mg of ammonium formate in 10 ml of methanol are microwave-heated at 80° C. (P 6-7 bar) for 5 min. The content of the tubes is combined and filtered on Clarcel. The Clarcel is washed with methanol and the filtrate is concentrated under vacuum. The residue is taken up with 20 ml of ethyl acetate, 2 ml of water and 8 ml of a saturated sodium chloride solution. The aqueous phase is extracted three times with 10 ml of ethyl acetate. The combined organic phases are washed with 10 ml of a saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated under vacuum, so as to obtain 1.053 g of 5-methyl-4-(4-methylpiperazin-1-yl)-2-(propan-2-yloxy)aniline in the form of a light brown solid.

후처리

  1. filtrationfiltered on Clarcel
  2. washThe Clarcel is washed with methanol
  3. concentrationthe filtrate is concentrated under vacuum
  4. extractionThe aqueous phase is extracted three times with 10 ml of ethyl acetate
  5. washThe combined organic phases are washed with 10 ml of a saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-59aec5fa4746428ca69c626cdecc2a1b
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115140B2

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