Ammonia → HCID 53754019, compound

HRID 343512Notes

Reaction equation

HRID 343512 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][C:6]([C:19]#[N:20])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:7][C:8](OCC)=[O:9])[CH3:2].C(O)C.[H][H].N>[Ni].C(OCC)C.CCCCCC>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][C:6]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7][C:8](=[O:9])[NH:20][CH2:19]1)[CH3:2]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 702EthanolHCID 54389077HCID 54389077, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 53754019HCID 53754019, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21584099Diethylether hexaneSolvent

Conditions

Temperature
50 °C

Procedure

Combine 3-cyano-3-phenylpentanedioic acid diethyl ester (93 g, 321 mmol) and ethanol (400 mL) in a 2 gallon pressure reactor. Add Raney nickel (280 g). Heat to 50° C. and charge with 200 psi of hydrogen. After 15 minutes, vent the reactor and add aqueous concentrated ammonia solution (120 mL). Charge the reactor with 200 psi of hydrogen. After 7 hours, vent the reactor and allow to stand for 18 hours. Filter through a celite pad and rinse the solids with ethanol. Evaporate the filtrate in vacuo to obtain a residue. Combine the residue and 1/5 diethyl ether/hexane (500 mL) and cool to -20° C. After 18 hours, decant and add 1/5 diethyl ether/hexane (500 mL) and cool to -20° C. to give a solid. Collect the solid by filtration and triturate with 1/5 diethyl ether/hexane (500 mL). Filter and dissolve in diethyl ether (300 mL) and add hexane (700 mL) to give a solid. Collect the solid by filtration and dry to give the title compound. Elemental Analysis calculated for C14H17NO3 : C 68.00; H 6.93; N 5.66; Found: C 67.63; H 6.99; N 5.81.

Workup

  1. waitAfter 7 hours
  2. waitto stand for 18 hours
  3. filtrationFilter through a celite pad
  4. washrinse the solids with ethanol
  5. customEvaporate the filtrate in vacuo
  6. customto obtain a residue
  7. temperaturecool to -20° C
  8. waitAfter 18 hours
  9. customdecant
  10. additionadd 1/5 diethyl ether/hexane (500 mL)
  11. temperaturecool to -20° C.
  12. customto give a solid
  13. customCollect the solid
  14. filtrationby filtration
  15. customtriturate with 1/5 diethyl ether/hexane (500 mL)
  16. filtrationFilter
  17. dissolutiondissolve in diethyl ether (300 mL)
  18. additionadd hexane (700 mL)
  19. customto give a solid
  20. customCollect the solid
  21. filtrationby filtration
  22. customdry

Sources & evidence

ORD record
ord-453a83e4f67a43c59867b57aa5a2fa63
Source dataset
uspto-grants-1999_01
Patent number
US05861417

Reaction notes

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