4-Piperidinecarboxamide → HCID 19008882, compound

HRID 2372312Notes

Reaction equation

HRID 2372312 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[N:3]=1.[NH:12]1[CH2:20][CH2:19][CH:15]([C:16]([NH2:18])=[O:17])[CH2:14][CH2:13]1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.CN(C=O)C>[F:9][C:8]([F:11])([F:10])[C:4]1[N:3]=[C:2]([N:12]2[CH2:20][CH2:19][CH:15]([C:16]([NH2:18])=[O:17])[CH2:14][CH2:13]2)[CH:7]=[CH:6][N:5]=1

Participants

6

Reactant 3

HCID 37724-PiperidinecarboxamideHCID 10340Sodium CarbonateHCID 152943694-Chloro-2-(trifluoromethyl)pyrimidine

Product 1

HCID 19008882HCID 19008882, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-chloro-2-(trifluoromethyl)pyrimidine (IV, 23.66 g, 0.130 mol), isonipecotamide (V, 16.66 g, 0.130 mol), and sodium carbonate (27.56 g, 0.260 mol) in acetonitrile (250 mL) was refluxed for 4 hr. The mixture was cooled and a solid mass formed. This mass was dissolved in DMF (300 mL) and filtered to remove the inorganics. The solvent was removed in vacuo and the crude product was recrystallized from isopropanol and then from 90% ethanol to give colorless needles (24.8 g, 70%).

Workup

  1. temperaturewas refluxed for 4 hr
  2. temperatureThe mixture was cooled
  3. customa solid mass formed
  4. filtrationfiltered
  5. customto remove the inorganics
  6. customThe solvent was removed in vacuo
  7. customthe crude product was recrystallized from isopropanol

Sources & evidence

ORD record
ord-e3e06cd3f8c9416bb0a7e8c92445aedb
Source dataset
uspto-grants-1992_03
Patent number
US05098904

Reaction notes

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