Potassium Carbonate → N-[1-(4-ethynylphenyl)ethyl]cyclopropylamine

HRID 1519698Notes

Reaction equation

HRID 1519698 reaction equation
C(=O)([O-])[O-].[K+].[K+].C[Si]([C:11]#[C:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([NH:21][CH:22]2[CH2:24][CH2:23]2)[CH3:20])=[CH:15][CH:14]=1)(C)C>CO>[C:12]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]([NH:21][CH:22]2[CH2:23][CH2:24]2)[CH3:20])=[CH:15][CH:14]=1)#[CH:11]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 71268174N-(1-{4-[(trimethylsilyl)ethynyl]phenyl}ethyl)cyclopropylamine

Product 1

HCID 86679268N-[1-(4-ethynylphenyl)ethyl]cyclopropylamineYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (96 mg) was added to a methanol (3.0 mL) solution of N-(1-{4-[(trimethylsilyl)ethynyl]phenyl}ethyl)cyclopropylamine (0.12 g) as obtained in Example 14-(2), and the mixture was stirred in a nitrogen atmosphere for 30 minutes at room temperature. After the solid was filtered out, the reaction mixture was concentrated. The resulting residue was purified by OH type silica gel chromatography (hexane/ethyl acetate=95/5) to obtain N-[1-(4-ethynylphenyl)ethyl]cyclopropylamine (colorless oil) (85 mg, 100%).

Workup

  1. filtrationAfter the solid was filtered out
  2. concentrationthe reaction mixture was concentrated
  3. customThe resulting residue was purified by OH type silica gel chromatography (hexane/ethyl acetate=95/5)

Sources & evidence

ORD record
ord-a8072e4f84c54e3d80da17bb30c6cf59
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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