Trifluoroacetic acid → 4-(3,4-Dichloro-phenyl)-3-methyl-1-(3-piperidin-1-yl-propyl)-piperazin-2-one
Reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11]([NH:16][CH:17]([CH3:36])[C:18]([N:20]([CH2:30][CH:31](OC)OC)[CH2:21][CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)=[O:19])[CH:12]=[CH:13][C:14]=1[Cl:15].C([SiH](CC)CC)C.C(N(CC)CC)C>C(Cl)Cl>[Cl:8][C:9]1[CH:10]=[C:11]([N:16]2[CH2:31][CH2:30][N:20]([CH2:21][CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[C:18](=[O:19])[CH:17]2[CH3:36])[CH:12]=[CH:13][C:14]=1[Cl:15]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Trifluoroacetic acid (1.15 g, 10.1 mmol) was added to a solution of 2-(3,4-dichloro-phenylamino)-N-(2,2-dimethoxy-ethyl)-N-(3-piperidin-1-yl-propyl)-propionamide (300 mg, 0.67 mmol) in CH2Cl2 (6 mL) at 0° C. After 30 min the ice bath was removed, then after 1 h triethylsilane (391 mg, 3.36 mmol) was added. After 16 h the reaction mixture was cooled to 0° C. and treated with triethylamine, then after 15 min partitioned between CH2Cl2 and sat. aq. NaHCO3 solution. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (IST Isolute® Flash NH2; EtOAc) afforded the title compound (184 mg, 71%). Yellow oil, MS: 384.2 (M+H)+.
Workup
- customAfter 30 min the ice bath was removed
- customafter 15 min partitioned between CH2Cl2 and sat. aq. NaHCO3 solution
- washThe organic layer was washed with brine
- dry with materialdried (MgSO4)
- customevaporated
Sources & evidence
- ORD record
- ord-a56f53edeb644ad0a47576be96b2d9f1
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08138175B2
Reaction notes
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