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Water → 2-[4-(2-hydroxyethyl)piperazin-1-yl]-N-[2,4 bis(2,2,2-trifluoroethoxy)-6-methylpyridin-3-yl]acetamide

HRID 2373676
Notes
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Reaction equation

HRID 2373676 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.Br[CH2:11][C:12]([NH:14][C:15]1[C:16]([O:28][CH2:29][C:30]([F:33])([F:32])[F:31])=[N:17][C:18]([CH3:27])=[CH:19][C:20]=1[O:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[O:13].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[F:31][C:30]([F:33])([F:32])[CH2:29][O:28][C:16]1[C:15]([NH:14][C:12](=[O:13])[CH2:11][N:7]2[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][OH:1])[CH2:5][CH2:6]2)=[C:20]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])[CH:19]=[C:18]([CH3:27])[N:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 76771-(2-Hydroxyethyl)piperazineHCID 11430Potassium CarbonateHCID 115899302-bromo-N-[2,4-bis(2,2,2-trifluoroethoxy)-6-methylpyridin-3-yl]acetamide

Product 1

HCID 231109552-[4-(2-hydroxyethyl)piperazin-1-yl]-N-[2,4 bis(2,2,2-trifluoroethoxy)-6-methylpyridin-3-yl]acetamideYield 91.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(2-Hydroxyethyl)piperazine (1.95 g, 15.0 mmol) and 2-bromo-N-[2,4-bis(2,2,2-trifluoroethoxy)-6-methylpyridin-3-yl]acetamide (5.00 g, 12.5 mmol) were dissolved in acetonitrile (30 mL). Potassium carbonate (2.25 g, 16.3 mmol) was added to the solution, followed by stirring for 5 hours at room temperature. The reaction mixture was dilluted with water, followed by extraction with ethyl acetate. The organic layer was sequentially washed with water and saturated brine, followed by drying over sodium sulfate anhydrate and concentration under reduced pressure. The obtained residue was purified through silica gel column chromatography (eluent: ammonia-saturated methanol/chloroform=1/20), to thereby yield 5.40 g of N-[2,4-bis(2,2,2-trifluoroethoxy)-6-methylpyridin-3-yl]-2-[4-(2-hydroxyethyl)piperazin-1-yl]acetamide as colorless crystals (yield 91%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was sequentially washed with water and saturated brine
  3. dry with materialby drying over sodium sulfate anhydrate and concentration under reduced pressure
  4. customThe obtained residue was purified through silica gel column chromatography (eluent: ammonia-saturated methanol/chloroform=1/20)

Sources & evidence

ORD record
ord-671738e2cbb344368e3704131c876b7b
Source dataset
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07459552B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes