Potassium Carbonate → N-(3-ethynyl-4-methoxyphenyl)-1-methylpiperidin-4-amine

HRID 1403213Notes

Reaction equation

HRID 1403213 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[CH:5][C:4]=1[C:17]#[C:18][Si](C)(C)C.C(=O)([O-])[O-].[K+].[K+]>CO>[C:17]([C:4]1[CH:5]=[C:6]([NH:9][CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])#[CH:18]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86725293N-{4-Methoxy-3-[(trimethylsilyl)ethynyl]phenyl}-1-methylpiperidin-4-amine

Product 1

HCID 71239579N-(3-ethynyl-4-methoxyphenyl)-1-methylpiperidin-4-amineYield 86.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-{4-methoxy-3-[(trimethylsilyl)ethynyl]phenyl}-1-methylpiperidin-4-amine (128 mg, 0.404 mmol) in methanol (2 mL) powdered anhydrous potassium carbonate (56 mg, 0.404 mmol) was added and the mixture was stirred at room temperature for 1 h. The solvent was removed under vacuum and the residue was taken up with EtOAc (30 mL). The solution obtained was washed with brine, (3×5 mL), water (5 m), dried over sodium sulfate and the solvent was removed under vacuum. The dark brown oil was purified by flash chromatography (EtOAc/MeOH/33% NH4OH 90/10/0.1) to yield the title compound as a yellow solid (85 mg, 86%).

Workup

  1. additionwas added
  2. customThe solvent was removed under vacuum
  3. customThe solution obtained
  4. washwas washed with brine, (3×5 mL), water (5 m)
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was removed under vacuum
  7. customThe dark brown oil was purified by flash chromatography (EtOAc/MeOH/33% NH4OH 90/10/0.1)

Sources & evidence

ORD record
ord-350625cf5c01486595bc7e253c647c0e
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

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