Ammonium formate → 4-(4-Benzyltriazol-2-yl)piperidine

HRID 1068172Notes

Reaction equation

HRID 1068172 reaction equation
[CH2:1]([C:8]1[CH:12]=[N:11][N:10]([CH:13]2[CH2:18][CH2:17][N:16](CC3C=CC=CC=3)[CH2:15][CH2:14]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])=O.[NH4+]>[Pd].CO>[CH2:1]([C:8]1[CH:12]=[N:11][N:10]([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 211931244-(4-Benzyltriazol-2-yl)-1-benzylpiperidine

Product 1

HCID 211930964-(4-Benzyltriazol-2-yl)piperidineYield 9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-(4-benzyltriazol-2-yl)-1-benzylpiperidine (627 mg, 1.9 mmol, from Step B), 10% palladium on carbon (400 mg, 0.38 mmol) and ammonium formate (770 mg, 11.3 mmol) in 20 mL MeOH was refluxed for 1 h. The mixture was filtered through celite and concentrated. The residue was dissolved in chloroform and the solution was washed with 1M aqueous NaOH. The organic layer was dried over Na2SO4 and concentrated to afford 41 mg (9%) of product was obtained which was used in the next step without purification.

Workup

  1. temperaturewas refluxed for 1 h
  2. filtrationThe mixture was filtered through celite
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in chloroform
  5. washthe solution was washed with 1M aqueous NaOH
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2d31414e75a44485bee1ef5a92631901
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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