Sodium Hydroxide → 1-(2-Chloro-benzenesulfonyl)-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid

HRID 2194115Notes

Reaction equation

HRID 2194115 reaction equation
C([O:3][C:4]([C:6]1([CH2:22][CH2:23][O:24][CH3:25])[CH2:11][CH2:10][N:9]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])(=[O:14])=[O:13])[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>CO>[Cl:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[S:12]([N:9]1[CH2:8][CH2:7][C:6]([CH2:22][CH2:23][O:24][CH3:25])([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]1)(=[O:13])=[O:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 667876761-(2-Chloro-benzenesulfonyl)-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 595780921-(2-Chloro-benzenesulfonyl)-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acidYield 111.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

1-(2-Chloro-benzenesulfonyl)-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester (0.5 g) was dissolved in MeOH (8 ml), 3M aqueous NaOH (6.41 ml) was added and the mixture was stirred at 5 h at 60° C. to complete the reaction. The solvent was evaporated off, the residue was acidified with 3M aqueous HCl and extracted with dichloromethane. The layers were separated, the organic phase was washed with brine, dried over sodium sulphate and concentrated to give the desired 1-(2-chloro-benzenesulfonyl)-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid (0.519 g) as a light brown solid. MS (ESI): 360.1 (M-H)−.

Workup

  1. customthe reaction
  2. customThe solvent was evaporated off
  3. extractionextracted with dichloromethane
  4. customThe layers were separated
  5. washthe organic phase was washed with brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-800c4c723c64418589bb6bd6c63a7c4a
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

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