Piperidine → Piperidine, 1-[3-(4-methoxyphenyl)-1-oxo-2-propenyl]-

HRID 2106806Notes

Reaction equation

HRID 2106806 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:7][O:8][C:9]1[CH:19]=[CH:18][C:12]([CH:13]=[CH:14][C:15](Cl)=[O:16])=[CH:11][CH:10]=1>C1C=CC=CC=1>[CH3:7][O:8][C:9]1[CH:19]=[CH:18][C:12]([CH:13]=[CH:14][C:15]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:16])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 534017724-Methoxycinnamic acid chloride

Product 1

HCID 762398Piperidine, 1-[3-(4-methoxyphenyl)-1-oxo-2-propenyl]-

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In a conical flask, 1.96 g of the paramethoxycinnamoyl chloride are dissolved in 20 ml of benzene. 2 ml of piperidine are added. After evaporation to dryness in vacuo, the residue is taken up in N hydrochloric acid and extracted with chloroform. The chloroform solution is washed successively with a 10% aqueous solution of KHCO3 and with water. It is then collected, dried over magnesium sulfate and evaporated. The product obtained is precipitated in cyclohexane and filtered off. After recrystallization from a 95° ethanol/water mixture (1/3:2/3), 2.15 g of white crystals are isolated (yield=78%).

Workup

  1. customAfter evaporation to dryness in vacuo
  2. extractionextracted with chloroform
  3. washThe chloroform solution is washed successively with a 10% aqueous solution of KHCO3 and with water
  4. customIt is then collected
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe product obtained
  8. customis precipitated in cyclohexane
  9. filtrationfiltered off
  10. customAfter recrystallization from a 95° ethanol/water mixture (1/3:2/3), 2.15 g of white crystals
  11. customare isolated (yield=78%)

Sources & evidence

ORD record
ord-848eb594e9134da5a8be0bd376d056b3
Source dataset
uspto-grants-1990_06
Patent number
US04931471

Reaction notes

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