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

HRID 83662

Reaktionsgleichung

Reaktionsgleichung von HRID 83662
[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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-425435ddcb2649c8b5d4b9e8fa4e60a2
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846684B2

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