Ethanol → 4-(Piperidine-1-sulfonyl)aniline

HRID 1984576

反応式

HRID 1984576 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+].C(O)C.NO>[Fe].O>[N:13]1([S:10]([C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=2)(=[O:12])=[O:11])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1

参加物

7

反応物 4

HCID 702EthanolHCID 787HydroxylamineHCID 25517Ammonium ChlorideHCID 7236241-[(4-Nitrophenyl)sulfonyl]piperidine

生成物 1

HCID 2366484-(Piperidine-1-sulfonyl)aniline

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 962Water溶媒

実験手順

1-(4-Nitro-benzenesulfonyl)-piperidine (30 g) was mixed with iron powder (50 g), ammonium chloride (50 g), ethanol (200 ml) and water (50 ml). The mixture was heated under reflux conditions for 2 h. LCMS showed that the reduction goes through a hydroxylamine intermediate. The mixture was filtered through Celite while hot and the iron residues washed with warm ethanol, ethyl acetate, water and dichloromethane. All volatiles were removed under reduced pressure and the residue partitioned between water and ethyl acetate. The organic solution was separated and washed with brine, dried over MgSO4 concentrated to give 4-(piperidine-1-sulfonyl)-phenylamine, 23 g. 1H NMR CDCl3 7.43 (2H, d), 6.67 (2H, d), 3.33 (2H, bs), 2.84 (4H, t), 1.53 (4H, m), 1.31 (2H, m)

後処理

  1. temperatureThe mixture was heated under reflux conditions for 2 h
  2. filtrationThe mixture was filtered through Celite while hot and the iron residues
  3. washwashed with warm ethanol, ethyl acetate, water and dichloromethane
  4. customAll volatiles were removed under reduced pressure
  5. customthe residue partitioned between water and ethyl acetate
  6. customThe organic solution was separated
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-b6d6f3b55af84e0fbb716a10748baaf5
出典データセット
uspto-grants-2009_06
特許番号
US07544702B2

関連ノート

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