Ammonium formate → 4-[N-(2-Hydroxy-3-piperidinopropyl)sulphamoyl]aniline

HRID 1071947노트

반응식

HRID 1071947 반응식
C([O-])=O.[NH4+].[OH:5][CH:6]([CH2:21][N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[CH2:7][NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1)(=[O:11])=[O:10]>[Pd].C(O)C>[OH:5][CH:6]([CH2:21][N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[CH2:7][NH:8][S:9]([C:12]1[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=1)(=[O:10])=[O:11]

참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 223906864-[N-(2-Hydroxy-3-piperidinopropyl)sulphamoyl]nitrobenzene

생성물 1

HCID 223905914-[N-(2-Hydroxy-3-piperidinopropyl)sulphamoyl]aniline수율 85%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매2회

실험 절차

Ammonium formate (1.1 g, 17.46 mmol) followed by a slurry of 10% palladium on carbon catalyst (0.7 g) in ethanol was added in portions to a suspension of 4-[N-(2-Hydroxy-3-piperidinopropyl)sulphamoyl]nitrobenzene (Method 117; 1.2 g, 3.5 mmol) in ethanol (100 ml). The mixture was heated at reflux under nitrogen for 2 hours. The mixture was cooled and the catalyst was removed by filtration through diatomaceous earth. The filter pad was washed with ethanol and the combined filtrates were evaporated. The residue was triturated with diethyl ether, collected by filtration and dried, to give the title compound (0.93 g, 85%) as a pale green solid. NMR: 1.3-1.5 (m, 6H), 2.10-2.32 (m, 6H), 2.60 (m, 1H), 2.75 (m, 1H), 3.52 (m, 1H), 4.50 (brs, 1H), 5.85 (s, 2H), 6.59 (d, 2H), 6.98 (brs, 1H), 7.39 (d, 2H); m/z: 314.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux under nitrogen for 2 hours
  3. temperatureThe mixture was cooled
  4. customthe catalyst was removed by filtration through diatomaceous earth
  5. washThe filter pad was washed with ethanol
  6. customthe combined filtrates were evaporated
  7. customThe residue was triturated with diethyl ether
  8. filtrationcollected by filtration
  9. customdried

출처 및 근거

ORD 기록
ord-9368b027c5f44e5aba3bcfe42575fdc3
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06908920B2

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