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

HRID 1984576

반응식

HRID 1984576 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 2366484-(Piperidine-1-sulfonyl)aniline

시약·촉매·용매 2

HCID 23925Iron촉매HCID 962Water용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-b6d6f3b55af84e0fbb716a10748baaf5
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544702B2

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