Water → HCID 70565633, compound

HRID 126932Notes

Reaction equation

HRID 126932 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[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:3]=[CH:4][C:5]([C:6]([N:8]([CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)[C@@H:9]2[CH2:13][N:12]([CH2:14][CH3:15])[CH2:11][C@H:10]2[OH:16])=[O:7])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 20288284HCID 20288284, compound

Product 1

HCID 70565633HCID 70565633, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6.9 g (0.014 mole) of trans-4-chlorobenzoic acid ester with 4-[(4-chlorobenzoyl)(cyclohexyl)amino]-1-ethyl-3-pyrrolidinol, 0.9 g (0.016 mole) of potassium hydroxide, 10 ml of water and 40 ml of methanol was heated on a steam bath for 1 hr. then concentrated to 10 ml volume under reduced pressure. The residue was partitioned between water and methylene chloride and the organic layer was dried and conentrated under reduced pressure. After recrystallization from 60% aqueous methanol, 3.5 g (72%) of white powder, m.p. 111°-116° C. was obtained.

Workup

  1. temperaturewas heated on a steam bath for 1 hr
  2. concentrationthen concentrated to 10 ml volume under reduced pressure
  3. customThe residue was partitioned between water and methylene chloride
  4. customthe organic layer was dried
  5. customAfter recrystallization from 60% aqueous methanol, 3.5 g (72%) of white powder
  6. customm.p. 111°-116° C. was obtained

Sources & evidence

ORD record
ord-08d4eef606664fa4b58704ae1afd6b93
Source dataset
uspto-grants-1981_03
Patent number
US04254135

Reaction notes

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