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

HRID 83662

반응식

HRID 83662 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-425435ddcb2649c8b5d4b9e8fa4e60a2
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846684B2

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