Hydrochloric Acid → HCID 19884924, compound

HRID 846200Notes

Reaction equation

HRID 846200 reaction equation
[CH3:1][N:2]([CH3:15])[CH:3]([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)[CH2:4][C:5]([OH:7])=[O:6].Cl.[CH2:17](O)[CH3:18]>>[CH3:15][N:2]([CH3:1])[CH:3]([C:8]1[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=1)[CH2:4][C:5]([O:7][CH2:17][CH3:18])=[O:6]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 19884918HCID 19884918, compound

Product 1

HCID 19884924HCID 19884924, compound

Procedure

A cold solution of 4.0 g of 3-dimethylamino-3-(4-fluorophenyl)propionic acid in 75 ml of ethanol was saturated with hydrogen chloride gas. The mixture was heated at reflux for approximately 16 hours and cooled to room temperature. The mixture was concentrated under vacuum and the residue was dissolved in water. The resulting mixture was washed with diethyl ether and the aqueous phase was made basic with 5N sodium hydroxide. The aqueous phase was extracted twice with diethyl ether and the ether extracts were combined, and washed with water, and a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The organic phase was concentrated under vacuum to provide 2.83 g of ethyl 3-dimethylamino-3-(4-fluorophenyl)propionate as an oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for approximately 16 hours
  3. concentrationThe mixture was concentrated under vacuum
  4. dissolutionthe residue was dissolved in water
  5. washThe resulting mixture was washed with diethyl ether
  6. extractionThe aqueous phase was extracted twice with diethyl ether
  7. washwashed with water
  8. dry with materiala saturated sodium chloride solution, and dried over anhydrous sodium sulfate
  9. concentrationThe organic phase was concentrated under vacuum

Sources & evidence

ORD record
ord-a1fba65ea2124a409d3b2783874dc442
Source dataset
uspto-grants-1992_08
Patent number
US05135947

Reaction notes

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