Potassium Carbonate → HCID 55297108, compound

HRID 1519726Notes

Reaction equation

HRID 1519726 reaction equation
C(=O)([O-])[O-].[K+].[K+].C[Si]([C:11]#[C:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2([NH2:22])[CH2:21][CH2:20]2)=[CH:15][CH:14]=1)(C)C>CO>[C:12]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2([NH2:22])[CH2:20][CH2:21]2)=[CH:15][CH:14]=1)#[CH:11]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 18378833HCID 18378833, compound

Product 1

HCID 55297108HCID 55297108, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (0.33 g) was added to a methanol (10 mL) solution of 1-{4-[(trimethylsilyl)ethynyl]phenyl}cyclopropylamine (0.37 g) as obtained in Example 21-(2), and the mixture was stirred for 1 hour at room temperature. After the potassium carbonate was filtered out and washed with chloroform, the solvent was distilled off under reduced pressure. The resulting residue was purified by OH type silica gel chromatography (gradient elution with hexane/AcOEt=70/30→30/70) to obtain 1-(4-ethynylphenyl)cyclopropylamine (Compound 404, yellow solid) (0.19 g, 76%).

Workup

  1. customas obtained in Example 21-(2)
  2. filtrationAfter the potassium carbonate was filtered out
  3. washwashed with chloroform
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting residue was purified by OH type silica gel chromatography (gradient elution with hexane/AcOEt=70/30→30/70)

Sources & evidence

ORD record
ord-ca7be48e61ab4c27858b1911ff9acbcc
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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