Methanol → 2-(Methyloxy)-4-[4-(methylsulfonyl)-1-piperazinyl]aniline

HRID 419644ノート

反応式

HRID 419644 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][N:15]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O.CO.[BH4-].[Na+]>C1COCC1.O.O.O.O.O.O.[Ni](Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][N:15]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[NH2:9]

参加物

6

反応物 3

HCID 887MethanolHCID 4311764Sodium borohydride2 回HCID 598602551-(3-Methoxy-4-nitro-phenyl)-4-methylsulfonyl-piperazine

生成物 1

HCID 598602722-(Methyloxy)-4-[4-(methylsulfonyl)-1-piperazinyl]aniline

試薬・触媒・溶媒 2

HCID 11791229Dichloronickel;hexahydrate触媒HCID 8028Tetrahydrofuran溶媒

実験手順

1-[3-(Methyloxy)-4-nitrophenyl]-4-(methylsulfonyl)piperazine (1.09 g, 3.46 mmol) was suspended in 5 mL THF and 10 mL MeOH in a 100 mL round bottom flask. Nickle(II)chloride hexahydrate (0.247 g, 1.04 mmol) was added followed by slow addition of NaBH4 (0.392 g, 10.38 mmol). TLC analysis indicated reaction complete after addition of NaBH4. Reaction mixture was adsorbed on SiO2 and purified via column chromatography using a gradient of 0-10% MeOH in DCM. Fractions were combined and rotovapped to give the title compound of step B. (0.925 g, 3.24 mmol, 93%); MS (ESI): 285 [M+H]+.

後処理

  1. customreaction
  2. customReaction mixture
  3. custompurified via column chromatography

出典と根拠

ORDレコード
ord-93280bf8391f478da0bd341a2fbbe156
出典データセット
uspto-grants-2012_01
特許番号
US08093239B2

反応ノート

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