Potassium Carbonate → (4-Ethynylphenyl)(4-methylpiperazin-1-yl)methanone

HRID 1403194Notes

Reaction equation

HRID 1403194 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]#[C:17][Si](C)(C)C)=[CH:12][CH:11]=2)=[O:9])[CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+]>CO>[C:16]([C:13]1[CH:12]=[CH:11][C:10]([C:8]([N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]2)=[O:9])=[CH:15][CH:14]=1)#[CH:17]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 71239568(4-Methylpiperazin-1-yl){4-[(trimethylsilyl)ethynyl]phenyl}methanone

Product 1

HCID 71239614(4-Ethynylphenyl)(4-methylpiperazin-1-yl)methanoneYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(4-Methylpiperazin-1-yl){4-[(trimethylsilyl)ethynyl]phenyl}methanone (1.29 g, 4.26 mmol) in MeOH (20 mL) was treated with solid K2CO3 (0.118 g, 0.85 mmol). After stirring at room temperature for 3 h the volatiles were removed by evaporation, the residue was taken up with DCM (40 mL), washed with water (30 mL), brine, dried over sodium sulfate and evaporated. The crude was purified by flash chromatography on silica gel (DCM/MeOH 95/5) to afford the title compound as white solid (0.690 g, 71%).

Workup

  1. customwere removed by evaporation
  2. washwashed with water (30 mL), brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe crude was purified by flash chromatography on silica gel (DCM/MeOH 95/5)

Sources & evidence

ORD record
ord-0ff30d7f8a3742d0af9f6f6eb54c4791
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

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