Triethylamine → 4-(2-Cyanophenyl)piperazine-1-carboxylic acid (3,5-bis-trifluoromethyl-phenyl)-amide

HRID 907568Notes

Reaction equation

HRID 907568 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)#[N:2].C(N(CC)CC)C.[F:22][C:23]([F:38])([F:37])[C:24]1[CH:25]=[C:26]([N:34]=[C:35]=[O:36])[CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1>ClCCl.O>[F:22][C:23]([F:37])([F:38])[C:24]1[CH:25]=[C:26]([NH:34][C:35]([N:12]2[CH2:13][CH2:14][N:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:1]#[N:2])[CH2:10][CH2:11]2)=[O:36])[CH:27]=[C:28]([C:30]([F:33])([F:31])[F:32])[CH:29]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27333143,5-Bis(trifluoromethyl)phenyl isocyanateHCID 2735875N-(2-Cyanophenyl)piperazine

Product 1

HCID 37992314-(2-Cyanophenyl)piperazine-1-carboxylic acid (3,5-bis-trifluoromethyl-phenyl)-amide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1-(2-Cyanophenyl)piperazine (1.0 g, 5.34 mmol) was dissolved in 25 mL of dichloromethane. Then, triethylamine (820 μL, 5.88 mmol) was added, followed by 3,5-bis(trifluoromethyl)phenyl isocyanate (1020 μL, 5.87 mmol). The reaction stirred at room temperature overnight. The reaction mixture was diluted with 50 mL of water and extracted three times with 25 mL portions of ethyl acetate. The combined organic fractions were washed twice with 25 mL of 0.1 M HCl, once with 25 mL of water, and once with 25 mL of saturated sodium bicarbonate. The organic fraction was dried with magnesium sulfate and concentrated under vacuum. The crude product was used without further purification.

Workup

  1. extractionextracted three times with 25 mL portions of ethyl acetate
  2. washThe combined organic fractions were washed twice with 25 mL of 0.1 M HCl, once with 25 mL of water
  3. dry with materialThe organic fraction was dried with magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe crude product was used without further purification

Sources & evidence

ORD record
ord-c508555fc04d48f7b36204b083ec3fd6
Source dataset
uspto-grants-2011_09
Patent number
US08013156B2

Reaction notes

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