Piperidine → HCID 54101561, compound

HRID 542167Notes

Reaction equation

HRID 542167 reaction equation
[C:1]([NH:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH3:13][CH:14]([C:19]([CH3:21])=[O:20])[CH2:15][C:16]([OH:18])=[O:17].N1CCCCC1>C1(C)C=CC=CC=1.O1CCCC1>[C:1]([NH:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH:21][C:19](=[O:20])[CH:14]([CH3:13])[CH2:15][C:16]([OH:18])=[O:17])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 8082PiperidineHCID 739424-AcetamidobenzaldehydeHCID 2465233-Methyl-4-oxopentanoic acid

Product 1

HCID 54101561HCID 54101561, compoundYield 51.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8.2 g (0.05 mol) of 4-acetamidobenzaldehyde, 7.2 g (0.055 mol) of β-methyl levulinic acid, 6.3 g (0.075 mol) of piperidine in a mixture of 125 ml of toluene and 75 ml of tetrahydrofuran is heated under relux with a Dean Stark apparatus for two hours. The solution is evaporated under vacuo and the residue is taken up with dilute aqueous K2CO3 solution. The insoluble material is extracted with ether and discarded. The pH of the solution is adjusted to 5.6 and the gummy material is extracted with ethyl acetate. The extract is washed with saturated sodium chloride solution, dried, and evaporated. The residue is crystallized from 2-propanol to give 7.1 g of 6-[4(acetylamino) phenyl]-3-methyl-4-oxo-5-hexenoic acid, mp 189°-190° C.

Workup

  1. temperatureis heated under relux with a Dean Stark apparatus for two hours
  2. customThe solution is evaporated under vacuo
  3. extractionThe insoluble material is extracted with ether
  4. extractionthe gummy material is extracted with ethyl acetate
  5. washThe extract is washed with saturated sodium chloride solution
  6. customdried
  7. customevaporated
  8. customThe residue is crystallized from 2-propanol

Sources & evidence

ORD record
ord-ae8266b77b694d6a8763c02cd6d3b132
Source dataset
uspto-grants-1987_04
Patent number
US04656170

Reaction notes

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