Hydrochloric Acid → 1-(4-Acetoxy-3-methoxycinnamoyl)piperidine

HRID 2225505Notes

Reaction equation

HRID 2225505 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7]([O:10][C:11]1[CH:21]=[CH:20][C:14]([CH:15]=[CH:16][C:17](Cl)=[O:18])=[CH:13][C:12]=1[O:22][CH3:23])(=[O:9])[CH3:8].Cl>N1C=CC=CC=1>[C:7]([O:10][C:11]1[CH:21]=[CH:20][C:14]([CH:15]=[CH:16][C:17]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:18])=[CH:13][C:12]=1[O:22][CH3:23])(=[O:9])[CH3:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 544680224-Acetoxy-3-methoxycinnamoyl chloride

Product 1

HCID 536775251-(4-Acetoxy-3-methoxycinnamoyl)piperidine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2 ml of piperidine was added to a solution of 5.09 g of 4-acetoxy-3-methoxycinnamoyl chloride in 100 ml of pyridine. The solution was reacted for hours at room temperature. After reaction, 200 ml of 2N hydrochloric acid was added to the reaction solution. The solution was extracted three times with 100 ml of ethyl acetate. The organic layer obtained was washed three times with 2N hydrochloric acid, twice with an aqueous sodium hydrogencarbonate solution and twice with an aqueous sodium chloride solution, and then was dried over magnesium sulfate. Thereafter, the solvent was removed in vacuo, and the product obtained was recrystallized from methylene chloride/hexane, yielding 1.88 g of 1-(4-acetoxy-3-methoxycinnamoyl)piperidine (a compound of the present invention) as pale yellowish white crystal, which had the following physiochemical properties:

Workup

  1. customThe solution was reacted for hours at room temperature
  2. additionwas added to the reaction solution
  3. extractionThe solution was extracted three times with 100 ml of ethyl acetate
  4. customThe organic layer obtained
  5. washwas washed three times with 2N hydrochloric acid
  6. dry with materialtwice with an aqueous sodium hydrogencarbonate solution and twice with an aqueous sodium chloride solution, and then was dried over magnesium sulfate
  7. customThereafter, the solvent was removed in vacuo
  8. customthe product obtained
  9. customwas recrystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-adae437650ea4ff98b5c345e62919113
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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