4-Methylphenyl isocyanate → 1-[[(4-Methylphenyl)amino]carbonyl]-4-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazine

HRID 1863025Notes

Reaction equation

HRID 1863025 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:19])=[CH:16][CH:15]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.[C:30]1([CH3:39])[CH:35]=[CH:34][C:33]([N:36]=[C:37]=[O:38])=[CH:32][CH:31]=1>C(Cl)Cl>[CH3:39][C:30]1[CH:35]=[CH:34][C:33]([NH:36][C:37]([N:23]2[CH2:24][CH2:25][N:20]([C:18](=[O:19])[C:17]3[CH:26]=[CH:27][C:14]([NH:13][C:7]4[C:6]5[C:11](=[CH:12][C:3]([C:2]([F:1])([F:28])[F:29])=[CH:4][CH:5]=5)[N:10]=[CH:9][CH:8]=4)=[CH:15][CH:16]=3)[CH2:21][CH2:22]2)=[O:38])=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 693254-Methylphenyl isocyanateHCID 30552431-Piperazinyl(4-((7-(trifluoromethyl)-4-quinolinyl)amino)phenyl)methanone

Product 1

HCID 135448611-[[(4-Methylphenyl)amino]carbonyl]-4-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazineYield 93%

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 p-tolyl isocyanate in 10 ml of methylene chloride under nitrogen at room temperature. After complete addition, the resultant suspension is stirred at room temperature for 2 hours. This suspension is then filtered and the white residue is washed with methylene chloride and dried. This is re-crystallized from methanol/methylene chloride to give 2.5 g (93%) of white crystalline 1-[[(4-methylphenyl)amino]carbonyl]-4-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazine of melting point 280°-282° C.

Workup

  1. additionAfter complete addition
  2. filtrationThis suspension is then filtered
  3. washthe white residue is washed with methylene chloride
  4. customdried
  5. customThis is re-crystallized from methanol/methylene chloride

Sources & evidence

ORD record
ord-eac2f1d105024ca5ab2919ad659b670d
Source dataset
uspto-grants-1979_09
Patent number
US04167567

Reaction notes

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