Allyl bromide → HCID 20071976, compound

HRID 1089302Notes

Reaction equation

HRID 1089302 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[C:11](=[O:12])[CH2:10][CH2:9][N:8]([C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:7]1)=[O:5])[CH3:2].[CH3:21][C:22]([O-])(C)[CH3:23].[K+].C(Br)C=C>C(O)(C)(C)C>[CH2:1]([O:3][C:4]([C:6]1([CH2:23][CH:22]=[CH2:21])[C:11](=[O:12])[CH2:10][CH2:9][N:8]([C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11277361HCID 11277361, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 20071976HCID 20071976, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

1.16 g (4.22 mmol) of ethyl-1-benzoyl-4-oxo-3-piperidine carboxylate, 9 ml of tert-butanol and 0.57 g (4.93 mmol) of potassium tert-butylate (97 percent) were used at 25° C. and stirred for 30 minutes. Then 0.70 g (5.67 mmol) of allylbromide was instilled in 2 minutes. The mixture was stirred with reflux for 16 hours, the reaction mixture was concentrated by evaporation and divided between 30 ml of methylene chloride and 30 ml of water. The emulsion was adjusted to pH 7 with hydrochloric acid (1N). The phases were separated and the aqueous phase was extracted three more times with 30 ml of methylene chloride. The combined organic phases was dried with magnesium sulfate and concentrated by evaporation. 1.34 g of crude product was obtained which was purified by column chromatography. The yield was 0.850 g of pure ethyl-1-benzoyl-4-oxo-3-(2-propenyl)-3-piperidine carboxylate, which equals 64 percent. Data concerning the compound was:

Workup

  1. customwere used at 25° C.
  2. stirringThe mixture was stirred
  3. temperaturewith reflux for 16 hours
  4. concentrationthe reaction mixture was concentrated by evaporation
  5. customThe phases were separated
  6. extractionthe aqueous phase was extracted three more times with 30 ml of methylene chloride
  7. dry with materialThe combined organic phases was dried with magnesium sulfate
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-33c82d6d93e94d1e83051db566a4bf39
Source dataset
uspto-grants-1990_10
Patent number
US04965359

Reaction notes

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