1-(3-(Trifluoromethyl)phenyl)piperazine → HCID 178506178, compound

HRID 1600683Notes

Reaction equation

HRID 1600683 reaction equation
Br[CH2:2][CH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11]2[N:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH2:6][CH2:5]1.[F:17][C:18]([F:32])([F:31])[C:19]1[CH:20]=[C:21]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:22]=[CH:23][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].C(#N)C>C(Cl)Cl>[N:12]1[CH:13]=[CH:14][CH:15]=[N:16][C:11]=1[NH:10][C@H:7]1[CH2:8][CH2:9][C@H:4]([CH2:3][CH2:2][N:28]2[CH2:27][CH2:26][N:25]([C:21]3[CH:22]=[CH:23][CH:24]=[C:19]([C:18]([F:31])([F:32])[F:17])[CH:20]=3)[CH2:30][CH2:29]2)[CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 42961-(3-(Trifluoromethyl)phenyl)piperazineHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 178419550HCID 178419550, compound

Product 1

HCID 178506178HCID 178506178, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of trans-[4-(2-Bromoethyl)-cyclohexyl]-pyrimidin-2-yl-amine (0.26 g, 0.91 mmol), 1-(3-trifluoromethyl-phenyl)-piperazine (0.21 g, 0.91 mmol), and potassium carbonate (0.21 g, 1.5 mmol) was heated in 10 mL refluxing acetonitrile for 18 hours. The reaction was diluted with methylene chloride, filtered, and the solvents were removed under reduced pressure. The residue was partitioned between chloroform and aqueous 2N sodium carbonate solution. The organic layer was dried over sodium sulfate and evaporated. The resulting residue was recrystallized from acetonitrile to give the title compound; mp 167° C.

Workup

  1. temperaturewas heated in 10 mL
  2. filtrationfiltered
  3. customthe solvents were removed under reduced pressure
  4. customThe residue was partitioned between chloroform and aqueous 2N sodium carbonate solution
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customevaporated
  7. customThe resulting residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-466884bff287421bb0018afb822f9a92
Source dataset
uspto-grants-1999_11
Patent number
US05977110

Reaction notes

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