Acetic Acid → HCID 68497728, compound

HRID 1038766Notes

Reaction equation

HRID 1038766 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12]3[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=3)=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:21]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)=[O:22].[CH:29](=O)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl>[CH2:29]([N:26]1[CH2:27][CH2:28][N:23]([C:21]([C:3]2[N:2]([CH3:1])[C:10]3[C:5]([CH:4]=2)=[CH:6][C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=2)=[CH:8][CH:9]=3)=[O:22])[CH2:24][CH2:25]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68494257HCID 68494257, compound

Product 1

HCID 68497728HCID 68497728, compoundYield 102.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of [1-methyl-5-(5-nitropyridin-2-yloxy)-1H-indol-2-yl]piperazin-1-ylmethanone (2.09 g, 5.5 mmol) in 1,2-dichloroethane (45 mL) were added benzaldehyde (1.16 g, 10 mmol), sodium triacetoxyborohydride (2.33 g, 11 mmol) and acetic acid (0.7 mL, 11 mmol) under ice cooling. The reaction mixture was stirred for 14 hours at room temperature under a nitrogen atomoshere. The solvent was removed under reduced pressure, and to the residue was added water. The mixture was neutralized with saturated aqueous NaHCO3 and extracted with AcOEt. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (CH2Cl2:MeOH=60:1) to give 2.66 g of the title compound as a pale brown oil.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionto the residue was added water
  3. extractionextracted with AcOEt
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (CH2Cl2:MeOH=60:1)

Sources & evidence

ORD record
ord-3606a21d5f63401aae119c384d17becf
Source dataset
uspto-grants-2013_10
Patent number
US08551999B2

Reaction notes

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