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

HRID 1071947ノート

反応式

HRID 1071947 の反応式
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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9368b027c5f44e5aba3bcfe42575fdc3
出典データセット
uspto-grants-2005_06
特許番号
US06908920B2

反応ノート

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