Acetic Acid → HCID 23285163, compound

HRID 2257145Notes

Reaction equation

HRID 2257145 reaction equation
C=O.[C:3]([BH3-])#N.[Na+].[CH2:7]([NH:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:33])[C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH:32]=[N:31][CH:30]=[N:29]3)=[CH:24][CH:23]=2)[CH2:17][CH2:16]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(O)(=O)C>CO>[CH3:3][N:14]([CH:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:33])[C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH:32]=[N:31][CH:30]=[N:29]3)=[CH:24][CH:23]=2)[CH2:17][CH2:16]1)[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 23285093HCID 23285093, compound

Product 1

HCID 23285163HCID 23285163, compoundYield 32.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.7 ml of a 37% aqueous formaldehyde solution and 0.21 g of sodium cyanoborohydride were added to 30 ml of a solution of 0.82 g of 4-benzylamino-1-[4-(1,2,4-triazol-1-yl)benzoyl]piperidine in methanol, under ice-cooling. To the mixture was dropwise added 0.7 ml of acetic acid. The mixture was stirred at room temperature for 1 hour and then subjected to distillation to remove the solvent. The residue was extracted with methylene chloride. The extract was washed with a 1N aqueous sodium hydroxide solution and water, dried with anhydrous magnesium sulfate, and then concentrated. The residue was purified by a silica gel column chromatography (eluant:methylene chloride/methanol=50/1), followed by recrystallization from methylene chloride-diethyl ether to obtain 0.28 g of 4-(N-methyl-N-benzylamino)-1-[4-(1,2,4-triazol-1-yl)benzoyl]piperidine as a white powder.

Workup

  1. temperaturecooling
  2. distillationsubjected to distillation
  3. customto remove the solvent
  4. extractionThe residue was extracted with methylene chloride
  5. washThe extract was washed with a 1N aqueous sodium hydroxide solution and water
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by a silica gel column chromatography (eluant:methylene chloride/methanol=50/1)
  9. customfollowed by recrystallization from methylene chloride-diethyl ether

Sources & evidence

ORD record
ord-d772d8da85de4535a6e58b7706c56c45
Source dataset
uspto-grants-1997_08
Patent number
US05656642

Reaction notes

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