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

HRID 1869941Notes

Reaction equation

HRID 1869941 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-b3356bde15784a118ae9a4c82854a1f8
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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