Acetic Acid → HCID 66571572, compound

HRID 83667Notes

Reaction equation

HRID 83667 reaction equation
[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.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.C([BH3-])#N.[Na+].C(O)(=O)C>CCO>[F:1][C:2]1[CH:3]=[CH:4][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[CH2:19][CH2:20][CH:21]([CH2:24][N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[CH2:22][CH2:23]2)=[O:17])=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 5003444Sodium cyanoborohydrideHCID 866718991-(1-(4-fluorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carbaldehyde

Product 1

HCID 66571572HCID 66571572, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(1-(4-fluorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carbaldehyde (52 mg, 0.143 mmol) was dissolved in EtOH (5 mL) and morpholine (0.025 mL, 0.285 mmol), sodium cyanoborohydride (18 mg, 0.285 mmol), and a catalytic drop of glacial acetic acid were added. Stirring was permitted for 13 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, 100% EtOAc.) The title compound was obtained as an oil. (Yield: 15 mg, 0.034 mmol, 24%) 1H NMR (400 MHz, CDCl3) 7.63, 7.37, 7.27-7.24, 7.14, 7.11-7.04, 6.91, 6.59, 5.47, 4.62, 4.09, 3.67, 2.74, 2.36, 2.08, 1.63, 0.96, 0.61

Workup

  1. customthe solvent was removed in vacuo
  2. washThe organic phase was washed with 10% aq. sodium carbonate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customPurification
  6. customwas obtained as an oil

Sources & evidence

ORD record
ord-1661c2ceead5416ba6b35031e4bdf050
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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