Trifluoroacetic acid → 5-[(Dimethylamino)methyl]-2H-1,2,3-triazole-4-carboxaldehyde

HRID 2303316Notes

Reaction equation

HRID 2303316 reaction equation
[NH:1]1[CH2:6]CCC[CH2:2]1.[C:7](O)(C(F)(F)F)=O.[NH:14]1[CH:18]=[C:17]([CH:19]=[O:20])[N:16]=[N:15]1>CC(O)C.O>[CH3:2][N:1]([CH2:6][C:18]1[C:17]([CH:19]=[O:20])=[N:16][NH:15][N:14]=1)[CH3:7]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8082PiperidineHCID 178519887HCID 178519887, compound

Product 1

HCID 98818305-[(Dimethylamino)methyl]-2H-1,2,3-triazole-4-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 21889133Propan-2-ol--water (1/1)Solvent

Conditions

Temperature
22.5 °C

Procedure

The piperidine adduct (62.1 g, 87 wt %, 54.0 g assay, 0.117 mol) was slurried in IPA/water (98:2, 365 mL). TFA (26.7 g, 18.0 mL, 0.234 mol) was added over 10 minutes maintaining the temperature at 20-25° C. The triazole aldehyde was liberated during the pH adjustment. The product crystallized from the reaction mixture.

Workup

  1. customThe product crystallized from the reaction mixture

Sources & evidence

ORD record
ord-8d1129c3b0204a568f76912a0042587f
Source dataset
uspto-grants-2002_08
Patent number
US06432952B1

Reaction notes

Loading…