Water → HCID 70563980, compound

HRID 126930Notes

Reaction equation

HRID 126930 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([N:8]([CH2:17][CH2:18][CH2:19][CH3:20])[CH:9]2[CH2:13][N:12]([CH2:14][CH3:15])[CH2:11][CH:10]2[OH:16])=[O:7])=[CH:4][CH:3]=1.[OH-].[K+].O>CO>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([N:8]([CH2:17][CH2:18][CH2:19][CH3:20])[C@@H:9]2[CH2:13][N:12]([CH2:14][CH3:15])[CH2:11][C@H:10]2[OH:16])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 20288298HCID 20288298, compound

Product 1

HCID 70563980HCID 70563980, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 7.0 g (0.015 mole) of trans-4-chlorobenzoic acid ester with 4-[(4-chlorobenzoyl)(n-butyl)amino]1-ethyl-3-pyrrolidinol, 0.9 g (0.016 mole) of potassium hydroxide, 15 ml of water and 60 ml of methanol was heated on a steam bath for 1 hr, then concentrated to approximately 10 ml volume under reduced pressure. The residue was partitioned between water and methylene chloride. The organic layer was separated, dried and concentrated under reduced pressure. The crystalline residue was recrystallized from isopropyl ether to give 4.3 g (89%) of white powder; m.p. 96.5°-98.0° C.

Workup

  1. temperaturewas heated on a steam bath for 1 hr
  2. concentrationconcentrated to approximately 10 ml volume under reduced pressure
  3. customThe residue was partitioned between water and methylene chloride
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe crystalline residue was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-8de27accfe274b6d9b52ca08c7b06d73
Source dataset
uspto-grants-1981_03
Patent number
US04254135

Reaction notes

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