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

HRID 2377411Notes

Reaction equation

HRID 2377411 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-8d24d4364adc48d597163253023cd505
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

Loading…