Water → HCID 86737535, compound

HRID 126931Notes

Reaction equation

HRID 126931 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[C:9]([N:17]([CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[CH:18]1[CH2:22][N:21]([CH2:23][CH3:24])[CH2:20][CH:19]1[OH:25])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-].[K+].O>CO>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[C:9]([N:17]([CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[C@@H:18]1[CH2:22][N:21]([CH2:23][CH3:24])[CH2:20][C@H:19]1[OH:25])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 20288275HCID 20288275, compound

Product 1

HCID 86737535HCID 86737535, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4.8 g (9 mmole) of trans-benzoic acid ester with 4-[(benzoyl)(cyclohexyl)amino]-1-ethyl-3-pyrrolidinol fumarate [1:1], 1.7 g (30 mmole) of potassium hydroxide, 10 ml of water and 40 ml of methanol was heated on a steam bath for 1 hr. then concentrated to approximately 5-10 ml volume under reduced pressure. The residue was partitioned between water and methylene chloride and the organic layer was dried and concentrated under reduced pressure. The residue was dissolved in ethyl acetate and 1.0 g fumaric acid added and the precipitate was collected. After recrystallization from ethyl acetate, 2.7 g (72%) of white powder, m.p. 145.0°-146.5° C. was obtained.

Workup

  1. temperaturewas heated on a steam bath for 1 hr
  2. concentrationthen concentrated to approximately 5-10 ml volume under reduced pressure
  3. customThe residue was partitioned between water and methylene chloride
  4. customthe organic layer was dried
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. addition1.0 g fumaric acid added
  8. customthe precipitate was collected
  9. customAfter recrystallization from ethyl acetate, 2.7 g (72%) of white powder
  10. customm.p. 145.0°-146.5° C. was obtained

Sources & evidence

ORD record
ord-650811b1609a4ee5bcb04cb636af2df7
Source dataset
uspto-grants-1981_03
Patent number
US04254135

Reaction notes

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