Acetic Acid → (1-(4-fluorobenzyl)-1H-indol-2-yl)(4-(((4-methylphenethyl)amino)methyl)piperidin-1-yl)methanone

HRID 83662

反応式

HRID 83662 の反応式
[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([CH:24]=O)[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1.[C:28]1([CH3:37])[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][NH2:36])=[CH:30][CH:29]=1.C([BH3-])#N.[Na+].C(O)(=O)C>C1COCC1>[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([CH2:24][NH:36][CH2:35][CH2:34][C:31]3[CH:32]=[CH:33][C:28]([CH3:37])=[CH:29][CH:30]=3)[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 76751p-MethylphenethylamineHCID 5003444Sodium cyanoborohydrideHCID 866718991-(1-(4-fluorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carbaldehyde

生成物 1

HCID 66571520(1-(4-fluorobenzyl)-1H-indol-2-yl)(4-(((4-methylphenethyl)amino)methyl)piperidin-1-yl)methanone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

1-(1-(4-fluorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carbaldehyde (46 mg, 0.126 mmol) was dissolved in THF (2 mL) and 2-(p-tolyl)ethanamine (0.030 mL, 0.189 mmol) was added. The solution was stirred at rt for 10 h, at which time the THF was removed in vacuo and the residue dissolved in EtOH (5 mL), and sodium cyanoborohydride (24 mg, 0.349 mmol) and a catalytic drop of glacial acetic acid were added. Stirring was permitted for 14 h, at which time the solvent was removed in vacuo, the residue was taken up in EtOAc. The organic phase was washed with 10% aq. sodium carbonate, dried over magnesium sulfate, and concentrated. Purification was accomplished via silica gel flash chromatography (30 g silica gel, 5:95 7M methanolic ammonia:ethyl acetate.) The title compound was obtained as a yellow oil. (Yield: 26 mg, 0.054 mmol, 43%) 1H NMR (400 MHz, CDCl3) 7.62, 7.36, 7.29-7.20, 7.17-7.07, 6.90, 6.58, 5.46, 4.62, 4.08, 2.89-2.65, 2.42, 2.31, 1.60, 1.01, 0.64

後処理

  1. customwas removed in vacuo
  2. dissolutionthe residue dissolved in EtOH (5 mL)
  3. customthe solvent was removed in vacuo
  4. washThe organic phase was washed with 10% aq. sodium carbonate
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customPurification
  8. customwas obtained as a yellow oil

出典と根拠

ORDレコード
ord-425435ddcb2649c8b5d4b9e8fa4e60a2
出典データセット
uspto-grants-2014_09
特許番号
US08846684B2

関連ノート

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