1-(3-(Trifluoromethyl)phenyl)piperazine → HCID 44197705, compound

HRID 2065533Notes

Reaction equation

HRID 2065533 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1.Cl.[C:31]1([CH:37]2[CH2:42][N:41]3[CH:43]=[C:44]([C:46]([OH:48])=O)[N:45]=[C:40]3[CH2:39][CH2:38]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[F:49][C:50]([F:64])([F:63])[C:51]1[CH:52]=[C:53]([N:57]2[CH2:62][CH2:61][NH:60][CH2:59][CH2:58]2)[CH:54]=[CH:55][CH:56]=1>CN(C=O)C>[C:31]1([CH:37]2[CH2:42][N:41]3[CH:43]=[C:44]([C:46]([N:60]4[CH2:59][CH2:58][N:57]([C:53]5[CH:54]=[CH:55][CH:56]=[C:51]([C:50]([F:63])([F:64])[F:49])[CH:52]=5)[CH2:62][CH2:61]4)=[O:48])[N:45]=[C:40]3[CH2:39][CH2:38]2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 42961-(3-(Trifluoromethyl)phenyl)piperazineHCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68908122HCID 68908122, compound

Product 1

HCID 44197705HCID 44197705, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

TBTU (276 mg; 0.86 mmol) and N-methylmorpholine (237 μl; 218 mg; 2.15 mmol) were added to a solution of 6-phenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid hydrochloride (200 mg; 0.72 mmol) in DMF (1 ml). The reaction mixture was stirred vigorously for 30 min at room temperature and then 1-(3-trifluoromethylphenyl)piperazine (162 μl; 198 mg; 0.86 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: 191 mg (59%).

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-96c40a73062b4f9fb2c9670b97f0ff7e
Source dataset
uspto-grants-2012_10
Patent number
US08288424B2

Reaction notes

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