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Potassium Iodide → 3-{2-[4-(4-Fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-6-methyl-pyridine-2-carbaldehyde

HRID 11694
Notes
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Reaction equation

HRID 11694 reaction equation
[OH:1][C:2]1[C:3]([CH:9]=[O:10])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.Cl[CH2:12][C:13]([N:15]1[CH2:20][C@H:19]([CH3:21])[N:18]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH2:17][C@H:16]1[CH3:30])=[O:14].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O.CCOC(C)=O>[F:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][N:18]2[C@@H:19]([CH3:21])[CH2:20][N:15]([C:13](=[O:14])[CH2:12][O:1][C:2]3[C:3]([CH:9]=[O:10])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=3)[C@H:16]([CH3:30])[CH2:17]2)=[CH:24][CH:25]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 113584612-Chloro-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanoneHCID 124219863-Hydroxy-6-methylpyridine-2-carbaldehyde

Product 1

HCID 865911663-{2-[4-(4-Fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-6-methyl-pyridine-2-carbaldehyde
Yield 120.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-hydroxy-6-methyl-pyridine-2-carbaldehyde (0.27 g, 1.95 mmol) in dimethylformamide (4 mL) was added 2-chloro-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone (0.53 g, 1.77 mmol), potassium carbonate (0.49 g, 3.5 mmol) and potassium iodide (0.29 g, 1.8 mmol). The resulting mixture was stirred at 60° C. overnight, then diluted with EtOAc, washed with brine and the organic layer was dried over magnesium sulfate. Filtration followed by concentration in vacuo gave the title compound (0.85 g)

Workup

  1. washwashed with brine
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. filtrationFiltration
  4. concentrationfollowed by concentration in vacuo

Sources & evidence

ORD record
ord-5b57c3e01bd9436dbaed9f98f84c2a35
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07098212B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes