Benzaldehyde → HCID 23285093, compound

HRID 369184Notes

Reaction equation

HRID 369184 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16](=[O:28])[C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH:27]=[N:26][CH:25]=[N:24]3)=[CH:19][CH:18]=2)[CH2:12][CH2:11]1.[BH4-].[Na+]>CO>[CH2:1]([NH:9][CH:10]1[CH2:11][CH2:12][N:13]([C:16](=[O:28])[C:17]2[CH:18]=[CH:19][C:20]([N:23]3[CH:27]=[N:26][CH:25]=[N:24]3)=[CH:21][CH:22]=2)[CH2:14][CH2:15]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 4311764Sodium borohydrideHCID 23285011HCID 23285011, compound

Product 1

HCID 23285093HCID 23285093, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

11.1 ml of benzaldehyde and 10 g of Molecular Sieve 3A were added to 50 ml of a solution of 2.97 g of 4-amino-1-[4-(1,2,4-triazol-1-yl)benzoyl]piperidine in methanol. The mixture was refluxed by heating, for 150 minutes. Thereto was added 4.97 g of sodium borohydride in small portions, under ice-cooling. The mixture was stirred for 1 hour under ice-cooling. The Molecular Sieve 3A was removed by filtration and the filtrate was subjected to distillation to remove the solvent. To the residue was added water. The mixture was made acidic with hydrochloric acid and then washed with ethyl acetate. The aqueous layer was made alkaline with an aqueous sodium hydroxide solution, under ice-cooling, followed by extraction with methylene chloride. The extract was washed with water, dried with anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (eluant: methylene chloride/methanol=50/1), followed by recrystallization from methylene chloride-ethyl acetate to obtain 2.92 g of 4-benzylamino-1-[4-(1,2,4-triazol-1-yl)benzoyl]piperidine as a white powder.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureby heating, for 150 minutes
  3. temperatureunder ice-cooling
  4. temperaturecooling
  5. customThe Molecular Sieve 3A was removed by filtration
  6. distillationthe filtrate was subjected to distillation
  7. customto remove the solvent
  8. additionTo the residue was added water
  9. washwashed with ethyl acetate
  10. temperatureunder ice-cooling
  11. extractionfollowed by extraction with methylene chloride
  12. washThe extract was washed with water
  13. dry with materialdried with anhydrous magnesium sulfate
  14. concentrationconcentrated
  15. customThe residue was purified by silica gel column chromatography (eluant: methylene chloride/methanol=50/1)
  16. customfollowed by recrystallization from methylene chloride-ethyl acetate

Sources & evidence

ORD record
ord-5c8bd2fe4cb34082ab886e7f84e52133
Source dataset
uspto-grants-2000_10
Patent number
US06136826

Reaction notes

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