1-(3-(Trifluoromethyl)phenyl)piperazine → HCID 44197706, compound

HRID 2065534Notes

Reaction equation

HRID 2065534 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1.Cl.[CH3:31][O:32][C:33]1[C:38]([CH3:39])=[CH:37][C:36]([CH:40]2[CH2:45][N:44]3[CH:46]=[C:47]([C:49](O)=[O:50])[N:48]=[C:43]3[CH2:42][CH2:41]2)=[CH:35][C:34]=1[CH3:52].[F:53][C:54]([F:68])([F:67])[C:55]1[CH:56]=[C:57]([N:61]2[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]2)[CH:58]=[CH:59][CH:60]=1>CN(C=O)C>[CH3:31][O:32][C:33]1[C:38]([CH3:39])=[CH:37][C:36]([CH:40]2[CH2:45][N:44]3[CH:46]=[C:47]([C:49]([N:64]4[CH2:63][CH2:62][N:61]([C:57]5[CH:58]=[CH:59][CH:60]=[C:55]([C:54]([F:67])([F:68])[F:53])[CH:56]=5)[CH2:66][CH2:65]4)=[O:50])[N:48]=[C:43]3[CH2:42][CH2:41]2)=[CH:35][C:34]=1[CH3:52]

Participants

6

Reactant 4

HCID 42961-(3-(Trifluoromethyl)phenyl)piperazineHCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68907890HCID 68907890, compound

Product 1

HCID 44197706HCID 44197706, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

TBTU (240 mg; 0.75 mmol) and N-methylmorpholine (206 μl; 189 mg; 1.87 mmol) were added to a solution of 6-(4-methoxy-3,5-dimethylphenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid hydrochloride (210 mg; 0.63 mmol) in DMF (1 ml). The reaction mixture was stirred vigorously for 30 min at room temperature and then 1-(3-trifluoromethylphenyl)piperazine (140 μl; 172 mg; 0.75 mmol) was added. The reaction mixture was stirred for 4 h at room temperature, then poured onto water and extracted with chloroform. The organic phase was dried over MgSO4, filtered and concentrated to small volume. The raw product was purified by column chromatography on silica gel (chloroform). Yield: 198 mg (62%).

Workup

  1. stirringThe reaction mixture was stirred for 4 h at room temperature
  2. additionpoured onto water
  3. extractionextracted with chloroform
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to small volume
  7. customThe raw product was purified by column chromatography on silica gel (chloroform)

Sources & evidence

ORD record
ord-6366eb30c2744154ba9459caa6ecaf56
Source dataset
uspto-grants-2012_10
Patent number
US08288424B2

Reaction notes

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