Potassium Carbonate → Cyclopropyl-(3-ethynyl-4-methylbenzyl)-methyl-amine

HRID 2377421Notes

Reaction equation

HRID 2377421 reaction equation
[CH:1]1([N:4]([CH3:19])[CH2:5][C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]#[C:14][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][C:9]([CH3:12])=[C:8]([C:13]#[CH:14])[CH:7]=2)[CH3:19])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 57424248Cyclopropyl-methyl-(4-methyl-3-trimethylsilanylethynyl-benzyl)-amine2×

Product 1

HCID 21107259Cyclopropyl-(3-ethynyl-4-methylbenzyl)-methyl-amineYield 96.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of cyclopropyl-methyl-(4-methyl-3-trimethylsilanylethynyl-benzyl)-amine (Intermediate 98, 0.95 g, 3.5 mmol) in methanol (10 mL) was treated with potassium carbonate (2.3 g, 16.6 mmol) and the resulting reaction mixture was stirred at ambient temperature for 1 h. 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 (0.67 g, 96%).

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-2913582fe2e8459594d0a42f7feffef3
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

Loading…