1-(3-(Trifluoromethyl)phenyl)piperazine → HCID 44197839, compound
Reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1.Cl.[F:31][C:32]1[CH:37]=[CH:36][C:35]([CH:38]2[CH2:43][N:42]3[CH:44]=[C:45]([C:47]([OH:49])=O)[N:46]=[C:41]3[CH2:40][CH2:39]2)=[CH:34][C:33]=1[CH3:50].[F:51][C:52]([F:66])([F:65])[C:53]1[CH:54]=[C:55]([N:59]2[CH2:64][CH2:63][NH:62][CH2:61][CH2:60]2)[CH:56]=[CH:57][CH:58]=1>CN(C=O)C>[F:31][C:32]1[CH:37]=[CH:36][C:35]([CH:38]2[CH2:43][N:42]3[CH:44]=[C:45]([C:47]([N:62]4[CH2:61][CH2:60][N:59]([C:55]5[CH:56]=[CH:57][CH:58]=[C:53]([C:52]([F:65])([F:66])[F:51])[CH:54]=5)[CH2:64][CH2:63]4)=[O:49])[N:46]=[C:41]3[CH2:40][CH2:39]2)=[CH:34][C:33]=1[CH3:50]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
TBTU (295 mg; 0.92 mmol) and N-methylmorpholine (253 μl; 232 mg; 2.3 mmol) were added to a solution of 6-(4-fluoro-3-methylphenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid hydrochloride (210 mg; 0.68 mmol) in DMF (1 ml). The reaction mixture was stirred vigorously for 30 min at room temperature and then 1-(3-trifluoromethylphenyl)piperazine (173 μl; 212 mg; 0.92 mmol) was added. The reaction mixture was stirred for 4 h at room temperature and poured onto water. The precipitated solid was purified by column chromatography on silica gel (chloroform). Yield: 166 mg (50%)
Workup
- stirringThe reaction mixture was stirred for 4 h at room temperature
- additionpoured onto water
- customThe precipitated solid was purified by column chromatography on silica gel (chloroform)
Sources & evidence
- ORD record
- ord-5c492f6b384c4fe894a26f674f54abba
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08288424B2
Reaction notes
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