Piperonal → HCID 68527102, compound

HRID 884166Notes

Reaction equation

HRID 884166 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([N:19]3[CH2:24][CH2:23][N:22]([CH2:25][C:26]4[CH:34]=[CH:33][C:32]5OCO[C:28]=5[CH:27]=4)[CH2:21][CH2:20]3)=[O:18])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[CH:35]1[C:40]([CH:41]=O)=[CH:39][C:38]2[O:43][CH2:44][O:45][C:37]=2[CH:36]=1.[BH4-].[Na+]>CO>[CH2:25]([N:22]1[CH2:23][CH2:24][N:19]([C:17](=[O:18])[CH2:16][CH2:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][C:5]3[CH:4]=[CH:3][C:2]([NH:1][CH2:41][C:40]4[CH:35]=[CH:36][C:37]5[O:45][CH2:44][O:43][C:38]=5[CH:39]=4)=[CH:7][N:6]=3)=[CH:10][CH:11]=2)[CH2:20][CH2:21]1)[C:26]1[CH:34]=[CH:33][CH:32]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 8438PiperonalHCID 4311764Sodium borohydrideHCID 68524377HCID 68524377, compound

Product 1

HCID 68527102HCID 68527102, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-[4-(5-aminopyridin-2-yloxy)phenyl]-1-(4-piperonylpiperazin-1-yl)propane-1-one (1.04 g, 2.5 mmol) was dissolved in methanol (25 mL). To the resulting solution was added piperonal (0.39 g, 2.63 mmol), and this solution was refluxed overnight. The resulting reaction solution was cooled with ice, and then sodium borohydride (0.28 g, 7.50 mmol) was added. The resulting solution was stirred for 2 hours at room temperature. This reaction solution was concentrated under reduced pressure. The residue was diluted with ethyl acetate, and washed with water, saturated sodium bicarbonate solution and brine. The organic layer was dried over anhydrous magnesium sulfate, and evaporated. The residue was then purified by silica gel column chromatography (ethyl acetate), to thereby yield 0.80 g of the title compound.

Workup

  1. temperaturethis solution was refluxed overnight
  2. customThe resulting reaction solution
  3. temperaturewas cooled with ice
  4. concentrationThis reaction solution was concentrated under reduced pressure
  5. additionThe residue was diluted with ethyl acetate
  6. washwashed with water, saturated sodium bicarbonate solution and brine
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. customevaporated
  9. customThe residue was then purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-79b7f744adea494c97891b6229e17b9f
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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