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

HRID 518825ノート

反応式

HRID 518825 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-59aec5fa4746428ca69c626cdecc2a1b
出典データセット
uspto-grants-2015_08
特許番号
US09115140B2

反応ノート

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