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Trifluoroacetic acid → 4-(3,4-Dichloro-phenyl)-3-methyl-1-(3-piperidin-1-yl-propyl)-piperazin-2-one

HRID 1096273
Notes
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Reaction equation

HRID 1096273 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 12052TriethylsilaneHCID 667831682-(3,4-Dichloro-phenylamino)-N-(2,2-dimethoxy-ethyl)-N-(3-piperidin-1-yl-propyl)-propionamide

Product 1

HCID 591592554-(3,4-Dichloro-phenyl)-3-methyl-1-(3-piperidin-1-yl-propyl)-piperazin-2-oneYield 71.5%

Reagents, catalysts & solvents

1
HCID 6344DichloromethaneSolvent

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

  1. customAfter 30 min the ice bath was removed
  2. customafter 15 min partitioned between CH2Cl2 and sat. aq. NaHCO3 solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-a56f53edeb644ad0a47576be96b2d9f1
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08138175B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes