Hydrochloric Acid → HCID 131727020, compound

HRID 30230Notes

Reaction equation

HRID 30230 reaction equation
FC(F)(F)C(O)=O.[C:8]1([CH:14]2[CH2:18][CH2:17][CH:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[NH:15]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+].[ClH:27]>C(OCC)C.O>[ClH:27].[C:19]1([CH:16]2[CH2:17][CH2:18][CH:14]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[NH:15]2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 21253969HCID 21253969, compound

Product 1

HCID 131727020HCID 131727020, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

Trifluoroacetic acid (10 ml) was added to 2,5-diphenylpyrrolidine (1.01 g, 3.13 minol) at 0° C. The mixture was stirred at 0° C. for 10 minutes, then the solvent was evaporated to afford a light brown solid to which was added 100 ml of water. To this solution was added 1N NaOH until pH=14 and the aqueous phase was extracted with chloroform. The organic phase was washed with 1N NaOH, water, brine and dried over MgSO4. After filtration and evaporation to dryness, the light-yellow solid obtained was dissolved in diethyl-ether. To this solution was added IN HCl (5 ml, 5 mmol), the precipitate obtained was collected by filtration, washed with diethyl-ether and dried under vacuum (0.590 g, 72.7%). 1H-NMR (CDCl3): δ ppm 7.30-7.60 (m, ArH, 10H), 4.95 (m, ArCH, 2H), 2.45-2.70 (m, CH2, 4H).

Workup

  1. customthe solvent was evaporated
  2. customto afford a light brown solid to which
  3. extractionthe aqueous phase was extracted with chloroform
  4. washThe organic phase was washed with 1N NaOH, water, brine
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration and evaporation to dryness
  7. customthe light-yellow solid obtained
  8. customthe precipitate obtained
  9. filtrationwas collected by filtration
  10. washwashed with diethyl-ether
  11. customdried under vacuum (0.590 g, 72.7%)

Sources & evidence

ORD record
ord-47ab686d713f488caaaf33b0d6d6fbea
Source dataset
uspto-grants-2008_09
Patent number
US07423059B2

Reaction notes

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