3-(Trifluoromethyl)phenyl isocyanate → HCID 20392870, compound

HRID 1863024Notes

Reaction equation

HRID 1863024 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][C:14]3[CH:27]=[CH:26][C:17]([C:18]([N:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)=O)=[CH:16][CH:15]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.[F:30][C:31]([F:42])([F:41])[C:32]1[CH:33]=[C:34]([N:38]=[C:39]=[O:40])[CH:35]=[CH:36][CH:37]=1>C(Cl)Cl>[F:30][C:31]([F:41])([F:42])[C:32]1[CH:33]=[C:34]([NH:38][C:39]([N:23]2[CH2:24][CH2:25][N:20]([CH2:18][C:17]3[CH:16]=[CH:15][C:14]([NH:13][C:7]4[C:6]5[C:11](=[CH:12][C:3]([C:2]([F:29])([F:1])[F:28])=[CH:4][CH:5]=5)[N:10]=[CH:9][CH:8]=4)=[CH:27][CH:26]=3)[CH2:21][CH2:22]2)=[O:40])[CH:35]=[CH:36][CH:37]=1

Participants

4

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 30552431-Piperazinyl(4-((7-(trifluoromethyl)-4-quinolinyl)amino)phenyl)methanone

Product 1

HCID 20392870HCID 20392870, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 4-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazine (2 g, 0.005 mol) in 15 ml of methylene chloride is added dropwise a solution of m-trifluoromethylphenyl isocyanate (0.935 g, 0.005 mol) in 10 ml of methylene chloride under nitrogen at room temperature. After complete addition, the resultant suspension is stirred at room temperature for 1 hour. This is then filtered and the white residue which is precipitated is washed with methylene chloride and dried. This is re-crystallized from methanol to give 2 g (68%) of white crystalline 1-[[[3-(trifluoromethyl)phenyl]amino]carbonyl]-4-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzyl]piperazine of melting point 198°-200° C.

Workup

  1. additionAfter complete addition
  2. filtrationThis is then filtered
  3. customthe white residue which is precipitated
  4. washis washed with methylene chloride
  5. customdried
  6. customThis is re-crystallized from methanol

Sources & evidence

ORD record
ord-c75de1beda9546b3bc9d2b57bc4ef098
Source dataset
uspto-grants-1979_09
Patent number
US04167567

Reaction notes

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