1,2-Dichloroethane → (4-Amino-2-(trifluoromethyl)phenyl)(4-ethylpiperazin-1-yl)methanone
Reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(CC)CC.[CH2:36]([N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1)[CH3:37]>C(Cl)Cl>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:41]2[CH2:42][CH2:43][N:38]([CH2:36][CH3:37])[CH2:39][CH2:40]2)=[O:8])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A mixture of 4-amino-2-trifluoromethyl-benzoic acid (15 g, 73.1 mmol), HOBT (14.56 g, 95 mmol), EDC (16.82 g, 88 mmol), Et3N (20.38 mL, 146 mmol), 1-ethyl-piperazine (8.35 g, 73.1 mmol) in DCM (200 mL) was stirred at 25° C. for 2 h. To the mixture was added DCM (200 mL) and then washed with H2O, 2 mol/L NaOH (2×150 mL) and brine. The organic layer was dried over Na2SO4 and concentrated to give a off white solid of (4-amino-2-trifluoromethyl-phenyl)-(4-ethyl-piperazin-1-yl)-methanone (20 g, 65.2 mmol, 89.0% yield): 1H NMR (400 MHz, CDCl3) δ: 7.07 (d, J=8.0 Hz, 1H), 6.92 (d, J=2.4 Hz, 1H), 6.79 (dd, J=2.0, 8.0 Hz, 1H), 3.99 (s, 2H), 3.84-3.76 (m, 2H), 3.25-3.23 (m, 2H), 2.50-2.39 (m, 4H), 2.33-2.31 (m, 2H), 1.08 (t, J=7.2 Hz, 3H); ES-LCMS m/z 302 (M+H).
Workup
- washwashed with H2O, 2 mol/L NaOH (2×150 mL) and brine
- dry with materialThe organic layer was dried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-245a17f3a9404d0ca4bd63b93db1e26f
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09035063B2
Reaction notes
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