Sodium Hydroxide → 2,2-Diphenyl-2-(pyrrolidin-3-yl)acetamide

HRID 1193977Notes

Reaction equation

HRID 1193977 reaction equation
C1(OC([N:10]2[CH2:14][CH2:13][CH:12]([C:15]([C:28]#[N:29])([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:11]2)=O)C=CC=CC=1.[OH-:30].[Na+]>S(=O)(=O)(O)O>[C:16]1([C:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([CH:12]2[CH2:13][CH2:14][NH:10][CH2:11]2)[C:28]([NH2:29])=[O:30])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 136337783-(Cyanodiphenylmethyl)-1-pyrrolidinecarboxylic acid phenyl ester

Product 1

HCID 136337542,2-Diphenyl-2-(pyrrolidin-3-yl)acetamideYield 65%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 3.0 g (0.008 mole) of 3-(cyanodiphenylmethyl)-1-pyrrolidinecarboxylic acid phenyl ester in 100 ml of 90% sulfuric acid was stirred at 70° C. for 20 hr. The reaction mixture was cooled, poured over ice and basified by adding, alternately, 50% sodium hydroxide and ice. The mixture was extracted with chloroform. The chloroform extract was washed with water, dried over sodium sulfate and concentrated in vacuo. The residue was crystallized in ethyl acetate. Recrystallization from ethyl acetate-ethanol gave 1.4 g (65%) of title product, molecular ion at 281 by mass spectrometer analysis.

Workup

  1. temperatureThe reaction mixture was cooled
  2. additionpoured over ice
  3. additionby adding
  4. extractionThe mixture was extracted with chloroform
  5. extractionThe chloroform extract
  6. washwas washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was crystallized in ethyl acetate
  10. customRecrystallization from ethyl acetate-ethanol

Sources & evidence

ORD record
ord-59f88556191948489f382b78aee5c680
Source dataset
uspto-grants-1989_03
Patent number
US04812452

Reaction notes

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