1,1,1,3,3,3-Hexafluoro-2-(4-((4-(4-nitrobenzylidene)piperidin-1-yl)methyl)phenyl)propan-2-ol → HCID 86670937、化合物

HRID 515280ノート

反応式

HRID 515280 の反応式
[F:1][C:2]([F:33])([F:32])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[CH2:21][CH2:20][C:19](=[CH:22][C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=3)[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].[H][H]>[Pd].C(OCC)(=O)C>[NH2:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][CH:19]2[CH2:18][CH2:17][N:16]([CH2:15][C:12]3[CH:13]=[CH:14][C:9]([C:3]([OH:8])([C:4]([F:7])([F:5])[F:6])[C:2]([F:1])([F:32])[F:33])=[CH:10][CH:11]=3)[CH2:21][CH2:20]2)=[CH:28][CH:27]=1

参加物

5

反応物 2

HCID 866709361,1,1,3,3,3-Hexafluoro-2-(4-((4-(4-nitrobenzylidene)piperidin-1-yl)methyl)phenyl)propan-2-olHCID 178418361HCID 178418361、化合物

生成物 1

HCID 86670937HCID 86670937、化合物収率 62.6%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

A stirred mixture of 1,1,1,3,3,3-hexafluoro-2-(4-((4-(4-nitrobenzylidene)piperidin-1-yl)methyl)phenyl)propan-2-ol (15.39 mmol, 7.3 g) and palladium on carbon (5%) (0.308 mmol, 0.328 g) in ethyl acetate was hydrogenated at 3 bar until the desired amount of hydrogen was consumed. The mixture was filtered through celite washing with ethyl acetate. The filtrate was concentrated under reduced pressure. The residue was chromatographed on silica (eluting with a gradient of dichloromethane to ethyl acetate) to give the title compound (4.3 g). MS (ESI) m/z 447.2 [M+H]+

後処理

  1. customwas consumed
  2. filtrationThe mixture was filtered
  3. washthrough celite washing with ethyl acetate
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was chromatographed on silica (
  6. washeluting with a gradient of dichloromethane to ethyl acetate)

出典と根拠

ORDレコード
ord-81b62cf1718e4f91bae9aa5a527b2a49
出典データセット
uspto-grants-2015_08
特許番号
US09108939B2

反応ノート

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