1-(3-(Trifluoromethyl)phenyl)piperazine → HCID 22602787, compound

HRID 2307844Notes

Reaction equation

HRID 2307844 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([NH2:10])=[O:9])=[CH:4][CH:3]=1.[F:11][C:12]([F:26])([F:25])[C:13]1[CH:14]=[C:15]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[F:26][C:12]([F:11])([F:25])[C:13]1[CH:14]=[C:15]([N:19]2[CH2:24][CH2:23][N:22]([C:2]3[N:7]=[CH:6][C:5]([C:8]([NH2:10])=[O:9])=[CH:4][CH:3]=3)[CH2:21][CH2:20]2)[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 42961-(3-(Trifluoromethyl)phenyl)piperazineHCID 10340Sodium CarbonateHCID 804566-Chloronicotinamide

Product 1

HCID 22602787HCID 22602787, compoundYield 9.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 6-chloro-3-pyridinecarboxamide (0.11 mol), 1-[3-(trifluoromethyl)-phenyl]-piperazine (0.1 mol) and sodium carbonate (0.22 mol) in DMF (300 ml) was stirred at 120° C. overnight. The mixture was poured out into ice water (600ml) and stirred for 1 hour. The precipitate was filtered off and dried Part of this fraction (4 g) was taken up in DCM and an aqueous NaHCO3 solution. The mixture was separated into its layers. The aqueous layer was extracted three times with DCM. The combined organic layer was dried, filtered and the solvent was evaporated till a small volume. The precipitate was filtered off and dried, yielding 3.2 g of 6-[4-[3-(trifluoromethyl)phenyl]-1-piperazinyl]-3-pyridinecarboxamide (intermediate 3).

Workup

  1. stirringstirred for 1 hour
  2. filtrationThe precipitate was filtered off
  3. customdried Part of this fraction (4 g)
  4. customThe mixture was separated into its layers
  5. extractionThe aqueous layer was extracted three times with DCM
  6. customThe combined organic layer was dried
  7. filtrationfiltered
  8. customthe solvent was evaporated till a small volume
  9. filtrationThe precipitate was filtered off
  10. customdried

Sources & evidence

ORD record
ord-9a2611f73e3e4024ac6b6000c14e98ea
Source dataset
uspto-grants-2004_12
Patent number
US06833369B2

Reaction notes

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