Toluene → HCID 68120624, compound

HRID 1414918Notes

Reaction equation

HRID 1414918 reaction equation
[C:1]1([C:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([CH:10]2[CH2:14][CH2:13][N:12]([CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:11]2)C#N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC=CC=1.[NH2-].[Na+].[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]\[C:37]([OH:39])=[O:38]>CCOCC.O>[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]\[C:37]([OH:39])=[O:38].[CH:7]([CH:10]1[CH2:14][CH2:13][N:12]([CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:11]1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 24533Sodium amideHCID 444266Maleic AcidHCID 21486053HCID 21486053, compound

Product 1

HCID 68120624HCID 68120624, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 41.3 g. (0.13 mole) of α,α-diphenyl-α-(1-isobutyl-3-pyrrolidinyl)acetonitrile in 120 ml. of dry toluene was added 11.2 g. (0.286 mole) of sodium amide in a 500 ml. round bottom flask equipped with a reflux condenser and mechanical stirrer. The stirred mixture was refluxed for 46 hours. A large excess of water was added slowly and the water layer separated and discarded after being extracted with ether which was combined with the organic layer. The organic layer was washed with water and extracted with an excess of 2 N hydrochloric acid. The acid extract was basified with sodium hydroxide and the oil which separated was extracted with ether. The ethereal solutions were combined, concentrated and the residue was distilled. Yield, 25.8 g. (68%); b.p. 150°-152° C/0.05 mm. To 11.2 g. (0.0382 mole) of the above product was added 4.45 g. (0.0382 mole) of maleic acid in 150 ml. of absolute alcohol. After the amine dissolved, 100 ml. of dry ether was added. On standing in the refrigerator for several days the solution yielded a white solid which was recrystallized from ethyl acetate. Yield, 10.5 g. (67.25%); m.p. 119°-120° C.

Workup

  1. customround bottom flask equipped with a reflux condenser and mechanical stirrer
  2. temperatureThe stirred mixture was refluxed for 46 hours
  3. customthe water layer separated
  4. extractionafter being extracted with ether which
  5. washThe organic layer was washed with water
  6. extractionextracted with an excess of 2 N hydrochloric acid
  7. extractionThe acid extract
  8. customthe oil which separated
  9. extractionwas extracted with ether
  10. concentrationconcentrated
  11. distillationthe residue was distilled
  12. customYield
  13. waitOn standing in the refrigerator for several days
  14. customthe solution yielded a white solid which
  15. customwas recrystallized from ethyl acetate
  16. customYield

Sources & evidence

ORD record
ord-e047a9b2aaa942c2b1d9c0cba3987738
Source dataset
uspto-grants-1977_01
Patent number
US04002766

Reaction notes

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