Ammonium formate → Diphenyl[1-(piperidin-4-ylmethyl)-1H-1,2,4-triazol-3-yl]methanol

HRID 2383383Notes

Reaction equation

HRID 2383383 reaction equation
[OH:1][C:2]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:3]1[N:7]=[CH:6][N:5]([CH2:8][CH:9]2[CH2:14][CH2:13][N:12](C(OCC3C=CC=CC=3)=O)[CH2:11][CH2:10]2)[N:4]=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[Pd+2].[OH-]>[C:31]1([C:2]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:3]2[N:7]=[CH:6][N:5]([CH2:8][CH:9]3[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]3)[N:4]=2)[OH:1])[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59145967Benzyl 4-({3-[hydroxy(diphenyl)methyl]-1H-1,2,4-triazol-1-yl}methyl)piperidine-1-carboxylate

Product 1

HCID 59145965Diphenyl[1-(piperidin-4-ylmethyl)-1H-1,2,4-triazol-3-yl]methanolYield 51%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Benzyl 4-({3-[hydroxy(diphenyl)methyl]-1H-1,2,4-triazol-1-yl}methyl)piperidine-1-carboxylate (Preparation 25, 5.2 g, 16.78 mmol) was dissolved in ethanol (300 ml) and ammonium formate (6 g) and palladium hydroxide [20 wt. % (dry basis) on carbon (wet)] (1 g) added. After stirring at reflux for 1 hour the reaction mixture was cooled to room temperature and filtered through Arbocel®. The solvent was removed in vacuo and the residue partitioned between dichloromethane (500 ml) and water (500 mL). The aqueous layer was separated and then basified with aqueous sodium hydroxide solution (2N, 200 ml) and extracted with dichloromethane (500 ml). This organic layer was then dried over magnesium sulphate, filtered and the solvent removed in vacuo. The crude material was recrystallised from acetonitrile to furnish the title compound as a white solid, in 51% yield, 1.9 g.

Workup

  1. temperatureat reflux for 1 hour the reaction mixture
  2. filtrationfiltered through Arbocel®
  3. customThe solvent was removed in vacuo
  4. customthe residue partitioned between dichloromethane (500 ml) and water (500 mL)
  5. customThe aqueous layer was separated
  6. extractionextracted with dichloromethane (500 ml)
  7. dry with materialThis organic layer was then dried over magnesium sulphate
  8. filtrationfiltered
  9. customthe solvent removed in vacuo
  10. customThe crude material was recrystallised from acetonitrile

Sources & evidence

ORD record
ord-ab31ea495b894b21ab51538d3834bf65
Source dataset
uspto-grants-2012_09
Patent number
US08263623B2

Reaction notes

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