Diphenylacetonitrile → HCID 21486052, compound

HRID 1414914Notes

Reaction equation

HRID 1414914 reaction equation
[NH2-].[Na+].[C:3]1([CH:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]#[N:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:18]([N:21]1[CH2:25][CH2:24][CH:23](Cl)[CH2:22]1)([CH3:20])[CH3:19]>C1(C)C=CC=CC=1>[C:12]1([C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)([CH:23]2[CH2:24][CH2:25][N:21]([CH:18]([CH3:20])[CH3:19])[CH2:22]2)[C:10]#[N:11])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 6837DiphenylacetonitrileHCID 24533Sodium amideHCID 19819749HCID 19819749, compound

Product 1

HCID 21486052HCID 21486052, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

In a 2 liter, three neck, round-bottom flask fitted with pot thermometer, reflux condensor, electric stirrer and dropping funnel was placed 47.5 g. (1.22 mole) of sodium amide followed by 300 ml. of dry toluene. To this was added dropwise at 50° C. 214 g. (1.11 mole) of diphenylacetonitrile in 800 ml. of dry toluene. When addition was complete, the temperature was raised slowly to reflux and maintained for 4 hours. To the refluxing mixture was added at a rapid dropwise rate 164.9 g. (1.11 mole) of 1-isopropyl-3-chloropyrrolidine. The refluxing and stirring was continued for 3 hours, and the mixture was allowed to stand overnight. The toluene solution was washed with 1 liter of water and extracted with about 2 liters of 1 N hydrochloric acid. The aqueous layer was made basic with dilute sodium hydroxide and extracted with several portions of ether. The ethereal solution was dried over sodium sulfate, concentrated, and the residue distilled through an eight inch beaded column. Yield, 216 g. (64%); b.p. 175°-177° C./0.25 mm. The product crystallized on standing and was recrystallized from iso-octane. m.p. 73°-74° C.

Workup

  1. customIn a 2 liter, three neck, round-bottom flask fitted with pot thermometer,
  2. temperaturereflux condensor, electric stirrer
  3. additionTo this was added dropwise at 50° C
  4. additionWhen addition
  5. temperaturethe temperature was raised slowly
  6. temperatureto reflux
  7. temperaturemaintained for 4 hours
  8. additionTo the refluxing mixture was added at a rapid dropwise rate 164.9 g
  9. waitto stand overnight
  10. washThe toluene solution was washed with 1 liter of water
  11. extractionextracted with about 2 liters of 1 N hydrochloric acid
  12. extractionextracted with several portions of ether
  13. dry with materialThe ethereal solution was dried over sodium sulfate
  14. concentrationconcentrated
  15. distillationthe residue distilled through an eight inch
  16. customYield
  17. customThe product crystallized
  18. customwas recrystallized from iso-octane

Sources & evidence

ORD record
ord-6e9ecf107efc4774878e5a2fec302031
Source dataset
uspto-grants-1977_01
Patent number
US04002766

Reaction notes

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