Dimethylamine, hydrochloride → HCID 69859264, compound

HRID 1634632Notes

Reaction equation

HRID 1634632 reaction equation
[CH:1]([CH:3]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])=O.Cl.[CH3:18][NH:19][CH3:20].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([C:3](=[CH:1][N:19]([CH3:20])[CH3:18])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 11106941HCID 11106941, compound

Product 1

HCID 69859264HCID 69859264, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

21 g (0.0945 mol) of ethyl α-formyl-p-methoxyphenylacetate, 80 ml of ethanol and 31,1 g (0.38 mol) of dimethylamine hydrochloride were mixed in a 250 ml balloon flask provided with magnetic stirring and thermometer under a gentle nitrogen flow. Subsequently 7.4 g (0.054 mol) of potassium carbonate were added. The thus obtained solution was stirred at room temperature for 3 days. The solvent was evaporated to dryness in the rotary evaporator and 120 ml of water were added over the thus obtained solid residue. The pH was adjusted to 5-6 with 5N hydrochloric acid and the product of the aqueous phase was extracted with 2×80 ml of dichloromethane. The organic extracts were dried with sodium sulfate and the solvent was removed under vacuum, to give a residue weighing 23.26 g and solidifying at room temperature (Yield: 98.7%)

Workup

  1. customprovided
  2. stirringThe thus obtained solution was stirred at room temperature for 3 days
  3. customThe solvent was evaporated to dryness in the rotary evaporator and 120 ml of water
  4. additionwere added over the thus obtained solid residue
  5. extractionthe product of the aqueous phase was extracted with 2×80 ml of dichloromethane
  6. dry with materialThe organic extracts were dried with sodium sulfate
  7. customthe solvent was removed under vacuum
  8. customto give a residue
  9. customat room temperature

Sources & evidence

ORD record
ord-927fa413dfa14345a439e8ba82833188
Source dataset
uspto-grants-2003_01
Patent number
US06506941B1

Reaction notes

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