Potassium Carbonate → 1-(4-Ethynyl-3-methoxyphenyl)-4-methylpiperazine

HRID 1403209Notes

Reaction equation

HRID 1403209 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)[CH:6]=[CH:7][C:8]=1[C:9]#[C:10][Si](C)(C)C.C(=O)([O-])[O-].[K+].[K+]>CO>[C:9]([C:8]1[CH:7]=[CH:6][C:5]([N:15]2[CH2:16][CH2:17][N:18]([CH3:21])[CH2:19][CH2:20]2)=[CH:4][C:3]=1[O:2][CH3:1])#[CH:10]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 867252923-Methoxy-4-[(trimethylsilyl)ethynyl]phenyl-4-methylpiperazine

Product 1

HCID 712395881-(4-Ethynyl-3-methoxyphenyl)-4-methylpiperazineYield 84.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-{3-methoxy-4-[(trimethylsilyl)ethynyl]phenyl-4-methylpiperazine (583 mg, 1.927 mmol) in anhydrous methanol (12 mL) is treated with powdered anhydrous potassium carbonate under stirring at room temperature for 1.5 h. After removing the solvent under vacuum the residue was taken up with EtOAc (80 mL) and water (5 mL). The phases were separated, the organic phase was washed with brine (3×10 mL), water (10 mL), dried over sodium sulfate and the solvent removed under vacuum. The dark oil obtained was purified by chromatography on silica gel (DCM/MeOH/TEA 90/10/0.1) to give the title compound as brownish solid (374 mg, 84.2%).

Workup

  1. customAfter removing the solvent under vacuum the residue
  2. customThe phases were separated
  3. washthe organic phase was washed with brine (3×10 mL), water (10 mL)
  4. dry with materialdried over sodium sulfate
  5. customthe solvent removed under vacuum
  6. customThe dark oil obtained
  7. customwas purified by chromatography on silica gel (DCM/MeOH/TEA 90/10/0.1)

Sources & evidence

ORD record
ord-a062148cf68948158b9cfee5bdb75259
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

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