Potassium Carbonate → (E)-N-ethyl-N-(6,6-dimethyl-2-hepten-4-ynyl)glycine hydrochloride

HRID 1464755Notes

Reaction equation

HRID 1464755 reaction equation
[ClH:1].[CH2:2]([NH:4][CH2:5]/[CH:6]=[CH:7]/[C:8]#[C:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH3:3].Br[CH2:15][C:16]([O:18]C)=[O:17].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>CN(C)C=O.CO.O>[ClH:1].[CH2:2]([N:4]([CH2:5]/[CH:6]=[CH:7]/[C:8]#[C:9][C:10]([CH3:12])([CH3:11])[CH3:13])[CH2:15][C:16]([OH:18])=[O:17])[CH3:3]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 60984Methyl bromoacetateHCID 19917114(E)-N-ethyl-6,6-dimethyl-2-hepten-4-ynylamine hydrochloride

Product 1

HCID 19917024(E)-N-ethyl-N-(6,6-dimethyl-2-hepten-4-ynyl)glycine hydrochlorideYield 114.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1.0 g of (E)-N-ethyl-6,6-dimethyl-2-hepten-4-ynylamine hydrochloride was dissolved in 20 ml of dimethylformamide, and 0.7 g of methyl bromoacetate and 1.0 g of potassium carbonate were added. The mixture was stirred overnight at room temperature, and worked up in a customary manner. The resulting glycine ester compound was dissolved in a methanol solution (50 ml) of 0.5 g of sodium hydroxide, and 25 ml of water was added. The mixture was stirred at room temperature for 2 hours, and the solvent was evaporated. The residue was dissolved in water, and the solution was made weakly acidic with hydrochloric acid, then butanol and a saturated aqueous solution of sodium chloride were added. The organic layer was separated and the solvent was evaporated, then the residue was dissolved in a 10% hydrogenchloridemethanol solution. The solvent was re-evaporated, and the residue was treated with hexane to give 1.36 g of the captioned compound as a pale yellow powder.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at room temperature for 2 hours
  3. customthe solvent was evaporated
  4. dissolutionThe residue was dissolved in water
  5. additionbutanol and a saturated aqueous solution of sodium chloride were added
  6. customThe organic layer was separated
  7. customthe solvent was evaporated
  8. dissolutionthe residue was dissolved in a 10% hydrogenchloridemethanol solution
  9. customThe solvent was re-evaporated
  10. additionthe residue was treated with hexane

Sources & evidence

ORD record
ord-5a06600d0dc447a6a45b22ca55d047fa
Source dataset
uspto-grants-1994_04
Patent number
US05306728

Reaction notes

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