Potassium Carbonate → HCID 71239669, compound

HRID 1403199Notes

Reaction equation

HRID 1403199 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][C:17]([C:20]#[C:21][Si](C)(C)C)=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+]>CO>[C:20]([C:17]1[CH:18]=[CH:19][C:14]([N:11]2[CH2:12][CH2:13][CH:8]([N:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)[CH2:9][CH2:10]2)=[CH:15][CH:16]=1)#[CH:21]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 71239606HCID 71239606, compound

Product 1

HCID 71239669HCID 71239669, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-methyl-4-(1-{4-[(trimethylsilyl)ethynyl]phenyl}piperidin-4-yl)piperazine (2.55 g, 7.179 mmol) in anhydrous methanol (25 mL) was treated with powdered anhydrous potassium carbonate (99.2 mg, 0.718 mmol) under stirring at room temperature for 3 h. After removing the solvent under vacuum the residue was taken up with DCM (50 mL) and water (5 mL). The phases were separated, the organic phase was washed with a saturated solution of sodium hydrogencarbonate (3×10 mL), brine (3×10 mL), water (10 mL), dried over sodium sulfate and the solvent removed under vacuum. The yellowish solid obtained was purified by chromatography on silica gel (DCM/MeOH/TEA 90/10/0.2) to give the title compound as yellow solid (1.534 g, 76%).

Workup

  1. customAfter removing the solvent under vacuum the residue
  2. customThe phases were separated
  3. washthe organic phase was washed with a saturated solution of sodium hydrogencarbonate (3×10 mL), brine (3×10 mL), water (10 mL)
  4. dry with materialdried over sodium sulfate
  5. customthe solvent removed under vacuum
  6. customThe yellowish solid obtained
  7. customwas purified by chromatography on silica gel (DCM/MeOH/TEA 90/10/0.2)

Sources & evidence

ORD record
ord-4109fe99ca054bf0b1ff6ef183c02b33
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

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