4-[[4-Methoxybenzenesulfonyl](benzyl)amino]-1-[benzyl]-4-[carbomethoxy]-piperidine → 4-[[4-Methoxybenzenesulfonyl](benzyl)amino]-1-[benzyl]-4-[carboxy]piperidine

HRID 264309Notes

Reaction equation

HRID 264309 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:13]2([C:26]([O:28]C)=[O:27])[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1>[OH-].[Na+].CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:13]2([C:26]([OH:28])=[O:27])[CH2:14][CH2:15][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:17][CH2:18]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 229070954-[[4-Methoxybenzenesulfonyl](benzyl)amino]-1-[benzyl]-4-[carbomethoxy]-piperidine

Product 1

HCID 229072304-[[4-Methoxybenzenesulfonyl](benzyl)amino]-1-[benzyl]-4-[carboxy]piperidine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A heterogeneous mixture of 4-[[4-methoxybenzenesulfonyl](benzyl)amino]-1-[benzyl]-4-[carbomethoxy]-piperidine (1.2 g, 2.26 mmol) in 50% aqueous sodium hydroxide (10 mL) and methanol (50 mL) is heated to reflux for 16 hours. The methanol is evaporated and the residue is neutralized with 4N hydrochloric acid. The aqueous solution is extracted with ethyl acetate. The combined organic extracts are dried (NaSO4) and the solvent is evaporated to give 4-[[4-methoxybenzenesulfonyl](benzyl)amino]-1-[benzyl]-4-[carboxy]-piperidine.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 16 hours
  3. customThe methanol is evaporated
  4. extractionThe aqueous solution is extracted with ethyl acetate
  5. dry with materialThe combined organic extracts are dried (NaSO4)
  6. customthe solvent is evaporated

Sources & evidence

ORD record
ord-de98e91535b84286bd891844d65cae53
Source dataset
uspto-grants-1997_07
Patent number
US05646167

Reaction notes

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