Piperidine → HCID 54536072, compound

HRID 868008Notes

Reaction equation

HRID 868008 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:4][C:3]1=2.[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]=O)[CH:18]=1.N1CCCCC1>C(O)(=O)C>[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]=[C:11]2[CH2:10][CH2:9][C:8]3[CH:7]=[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:4][C:3]=3[C:2]2=[O:1])[CH:18]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 103713-PyridinecarboxaldehydeHCID 13607596Ethyl 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate

Product 1

HCID 54536072HCID 54536072, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

5.0 g of ethyl 5-oxo-5,6,7,8-tetrahydro-2-naphthalenecarboxylate was mixed with 2.5 g of 3-pyridinealdehyde, 10 ml of acetic acid and 10 ml of piperidine and then the mixture was stirred at 100° C. for 4 hours. The reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate. 10% Hydrochloric acid was added to the solution. The aqueous layer was separated and neutralized by addition of sodium bicarbonate. The mixture was extracted with chloroform. The extract was washed with water, dried and then concentrated in vacuo. The residue was purified by silica gel column chromatography to give 5.6 g of ethyl 6-(3-pyridylmethylidene)-5-oxo-5,6,7,8-tetrahydro-2-naphthalenecarboxylate as pale yellow crystals with m.p. 112°-114° C.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. addition10% Hydrochloric acid was added to the solution
  4. customThe aqueous layer was separated
  5. additionneutralized by addition of sodium bicarbonate
  6. extractionThe mixture was extracted with chloroform
  7. washThe extract was washed with water
  8. customdried
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-92719ea9d3784d19a7fbd9a323175854
Source dataset
uspto-grants-1988_10
Patent number
US04777257

Reaction notes

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