Potassium Carbonate → HCID 10878074, compound

HRID 1288251Notes

Reaction equation

HRID 1288251 reaction equation
[C:1]([CH:6]1[CH2:11][CH2:10][CH2:9][NH:8][C:7]1=O)([O:3][CH2:4][CH3:5])=[O:2].F[B-](F)(F)F.C([O+](CC)CC)C.C(=O)([O-])[O-].[K+].[K+].Br.Br[CH2:33][CH2:34][NH2:35].C[O-].[Na+]>C(Cl)Cl.C(O)C>[NH:35]1[C:7]2=[C:6]([C:1]([O:3][CH2:4][CH3:5])=[O:2])[CH2:11][CH2:10][CH2:9][N:8]2[CH2:33][CH2:34]1

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 977733-Carbethoxy-2-piperidoneHCID 2723982Triethyloxonium tetrafluoroborateHCID 27742172-Bromoethylamine hydrobromideHCID 10942334Sodium Methoxide

Product 1

HCID 10878074HCID 10878074, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-carboethoxy-2-piperidone (25 g., 0.15 mole) in methylenechloride (150 ml.) is added dropwise with stirring at 0° C. to a solution of triethyloxonium fluoroborate (29 g.) in methylenechloride (150 ml.). After stirring for six hours, 33 g. of a 50% aqueous potassium carbonate solution is added and the organic layer is separated, dried over anhydrous K2CO3, filtered and concentrated under reduced pressure. Distillation of the concentrate gives 7.1 g. of the lactam ether, b.p. 90°/5 mm. which is dissolved in 100 ml. of ethanol containing 2-bromoethylamine hydrobromide (7.1 g., 0.035 mole). The solution is stirred for two days at room temperature. To this solution is added 2.1 g. of sodium methoxide. The solution is heated under reflux for one hour and then evaporated. The residue is treated with aqueous sodium hydroxide and extracted with chloroform. The chloroform solution is dried over Na2SO4, filtered and the filtrate evaporated. Distillation of the residue gives 3.5 g. of product b.p. 14°-5°/0.2 mm. which crystallizes on standing, m.p. 89°-02° C.

Workup

  1. customthe organic layer is separated
  2. dry with materialdried over anhydrous K2CO3
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. distillationDistillation of the concentrate
  6. customgives 7.1 g
  7. dissolutionwhich is dissolved in 100 ml
  8. stirringThe solution is stirred for two days at room temperature
  9. additionTo this solution is added 2.1 g
  10. temperatureThe solution is heated
  11. temperatureunder reflux for one hour
  12. customevaporated
  13. additionThe residue is treated with aqueous sodium hydroxide
  14. extractionextracted with chloroform
  15. dry with materialThe chloroform solution is dried over Na2SO4
  16. filtrationfiltered
  17. customthe filtrate evaporated
  18. distillationDistillation of the residue
  19. customgives 3.5 g
  20. customwhich crystallizes

Sources & evidence

ORD record
ord-470a67cc22284161b5d5f22829a0b031
Source dataset
uspto-grants-1976_10
Patent number
US03987183

Reaction notes

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