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

HRID 2253901Notes

Reaction equation

HRID 2253901 reaction equation
[C:1]([C:3]([CH:16]1[CH2:20][CH2:19][NH:18][CH2:17]1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)#[N:2].[OH-:21].[Na+]>S(=O)(=O)(O)O.O>[C:1]([C:3]([CH:16]1[CH2:20][CH2:19][NH:18][CH2:17]1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:21])[NH2:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 13633741Diphenyl(pyrrolidin-3-yl)acetonitrile

Product 1

HCID 136337542,2-Diphenyl-2-(pyrrolidin-3-yl)acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
85 °C

Procedure

3-(R,S)-(1-Cyano-1,1-diphenylmethyl)pyrrolidine (30 g-see Preparation 7) was dissolved in 95% sulphuric acid (210 ml) and the mixture was heated, with stirring, at 85° C. for 9 hours and then at 100° C. for 30 minutes. The mixture was allowed to cool to room temperature and poured onto ice (2 kg). The mixture was basified (pH 12) by addition, in portions with cooling in an ice bath, of a cold solution of sodium hydroxide (340 g) in water (500 ml). The resulting mixture was extracted with dichloromethane (3×300 ml) and the combined extracts were dried (MgSO4) and concentrated in vacuo to give the title compound as a foam, yield 16.4 g.

Workup

  1. temperaturethe mixture was heated
  2. waitat 100° C. for 30 minutes
  3. temperatureto cool to room temperature
  4. additionpoured onto ice (2 kg)
  5. additionby addition
  6. extractionThe resulting mixture was extracted with dichloromethane (3×300 ml)
  7. dry with materialthe combined extracts were dried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1e64768965c84249b4578b927c7b2a87
Source dataset
uspto-grants-1993_08
Patent number
US05233053

Reaction notes

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