Sodium Hydroxide → Cyclohexanecarboxylic Acid (4-hydroxy-benzyl)-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amide

HRID 1827524Notes

Reaction equation

HRID 1827524 reaction equation
[CH:1]1([C:7]([N:9]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31]S(C3C=CC(C)=CC=3)(=O)=O)=[CH:27][CH:26]=2)[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:12][CH:11]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO>[OH:31][C:28]1[CH:27]=[CH:26][C:25]([CH2:24][N:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:12][CH:11]=2)[C:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:8])=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86592782HCID 86592782, compound

Product 1

HCID 9845153Cyclohexanecarboxylic Acid (4-hydroxy-benzyl)-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amideYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of toluene-4-sulfonic acid 4-({cyclohexanecarbonyl-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amino}-methyl)-phenyl ester in 5 mL methanol was added 5N NaOH (0.50 mL). The reaction mixture was heated at reflux until complete as judged by TLC and MS. The reaction mixture was washed with methylene chloride. The organic layer was concentrated to afford 0.045 g (41%) of the title compound. MS 423.2 (M+1)+

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux until complete
  3. washThe reaction mixture was washed with methylene chloride
  4. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-abf7434e026f4f52ad0fa1985d643c6c
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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