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

HRID 1014344ノート

反応式

HRID 1014344 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>[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

5

反応物 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 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 1

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. NiCl2-6H2O (0.247 g, 1.04 mmol) was added, followed by slow addition of NaBH4 (0.392 g, 10.38 mmol). The reaction mixture was adsorbed on SiO2 and purified via column chromatography to afford 2-(methyloxy)-4-[4-(methylsulfonyl)-1-piperazinyl]aniline. (0.925 g, 3.24 mmol, 93%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.91 (s, 3 H) 2.99-3.07 (m, 4 H) 3.19-3.27 (m, 4 H) 3.75 (s, 3 H) 4.28 (s, 2 H) 6.33 (dd, J=8.39, 2.43 Hz, 1 H) 6.49-6.58 (m, 2 H). ESIMS M+H)+=285.

後処理

  1. custompurified via column chromatography

出典と根拠

ORDレコード
ord-0d39f6e85ff841e68ea5e7f37a57c34f
出典データセット
uspto-grants-2011_07
特許番号
US07981903B2

反応ノート

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