Hydrochloric Acid → HCID 19426621, compound

HRID 741572Notes

Reaction equation

HRID 741572 reaction equation
[N:1]1([CH2:14][CH2:15][C:16]([O:18]CC)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][CH2:8]C(OCC)=O.[H-].[Na+].C(O)C.Cl>C1(C)C(C)=CC=CC=1>[N:1]12[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][CH2:8][C:16](=[O:18])[CH2:15][CH2:14]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 24758Sodium hydrideHCID 19426626HCID 19426626, compound

Product 1

HCID 19426621HCID 19426621, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent3×

Procedure

A solution of diethyl piperidine-1,2-dipropionate (9.60 g, 0.034 mole) in xylene (100 ml) was added dropwise over 4 h to a flask containing 250 ml of xylene, which was being fed via a continuous extraction apparatus to a stirred, refluxing, suspension of sodium hydride (4.2 g of 80%, 0.14 mole) in xylene (100 ml) containing ethanol (0.5 ml) under nitrogen. The reaction mixture was heated under reflux for a total of 40 h, then cooled in an ice bath and treated with 5M HCl acid (250 ml). The aqueous layer was separated, treated with concentrated HCl acid (30 ml) and heated under reflux for 18 h. The solution was cooled, basified with potassium carbonate and extracted with ether (3×100 ml). The combined extracts were dried (Na2CO3), concentrated in vacuo and the residue distilled in a Kugelr ohr apparatus to give the title compound as a colourless oil (4.6 g, 84%) bp approx. 110° C. at 0.25 mm Hg.

Workup

  1. temperaturerefluxing
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for a total of 40 h
  4. temperaturecooled in an ice bath
  5. customThe aqueous layer was separated
  6. additiontreated with concentrated HCl acid (30 ml)
  7. temperatureheated
  8. temperatureunder reflux for 18 h
  9. temperatureThe solution was cooled
  10. extractionextracted with ether (3×100 ml)
  11. dry with materialThe combined extracts were dried (Na2CO3)
  12. concentrationconcentrated in vacuo
  13. distillationthe residue distilled in a Kugelr ohr apparatus

Sources & evidence

ORD record
ord-cb09f544e4fa4f38bcfa2d7ff00a78db
Source dataset
uspto-grants-1996_09
Patent number
US05552398

Reaction notes

Loading…