Potassium Carbonate → Cyclopropyl-(3-ethynyl-benzyl)-methyl-amine

HRID 1869931Notes

Reaction equation

HRID 1869931 reaction equation
[CH:1]1([N:4]([CH3:18])[CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([C:12]#[C:13][Si](C)(C)C)[CH:7]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH:1]1([N:4]([CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([C:12]#[CH:13])[CH:7]=2)[CH3:18])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 57424247Cyclopropyl-methyl-(3-trimethylsilanylethynyl-benzyl)-amine2×

Product 1

HCID 21107260Cyclopropyl-(3-ethynyl-benzyl)-methyl-amineYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution cyclopropyl-methyl-(3-trimethylsilanylethynyl-benzyl)-amine (Intermediate 90, 0.355 g, 1.38 mmol) in methanol (10 mL) was treated with potassium carbonate (0.13 g, 0.95 mmol) and the resulting reaction mixture was stirred at ambient temperature overnight. The solvent was evaporated in vacuo, the residue was diluted with water and extracted with diethyl ether. The organic phase was washed with brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title compound (0.22 g, 86%).

Workup

  1. customthe resulting reaction mixture
  2. customThe solvent was evaporated in vacuo
  3. additionthe residue was diluted with water
  4. extractionextracted with diethyl ether
  5. washThe organic phase was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-b55ffacaa83f4ce3a82fa5145f659afd
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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