Hydrochloric Acid → HCID 22097575, compound

HRID 1458899Notes

Reaction equation

HRID 1458899 reaction equation
C(O)(C(F)(F)F)=O.[CH2:8]([C:11]1([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)[CH:9]=[CH2:10].Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].C([O-])([O-])=O.[K+].[K+].Cl>C1(C)C=CC=CC=1>[CH2:8]([C:11]1([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:16][CH2:15][N:14]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:13][CH2:12]1)[CH:9]=[CH2:10]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 22097570HCID 22097570, compound

Product 1

HCID 22097575HCID 22097575, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

The crude TFA salt of ethyl 4-allyl-isonipecotate and ethyl bromoacetate (23.5 g, 141 mmol) were dissolved in toluene. To this solution was added anhydrous K2CO3 (70.7 g, 512 mmol), and the resulting suspension was warmed to 80° C. for 15 minutes. The reaction mixture was cooled down, and adjusted at pH=8.0 with dil.HCl. The resulting solution was worked-up by an ordinal procedure (extraction with ethyl acetate, washing with brine, drying over Na2SO4, concentration by evaporation) to provide 37.4 g of crude ethyl 4-allyl-N-ethoxycarbonylmethyl-isonipecotate, 56.

Workup

  1. temperatureThe reaction mixture was cooled down
  2. extractionThe resulting solution was worked-up by an ordinal procedure (extraction with ethyl acetate, washing with brine, drying over Na2SO4, concentration by evaporation)

Sources & evidence

ORD record
ord-a72ba7914b034a1a8599606dc79530bf
Source dataset
uspto-grants-1998_12
Patent number
US05852038

Reaction notes

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