Sodium Hydroxide → 1-(morpholin-4-ylsulfonyl)piperidine-4-carboxylic acid

HRID 2381180Notes

Reaction equation

HRID 2381180 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([S:12]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)(=[O:14])=[O:13])[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>CO>[N:15]1([S:12]([N:9]2[CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]2)(=[O:14])=[O:13])[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 3422241HCID 3422241, compound

Product 1

HCID 32397731-(morpholin-4-ylsulfonyl)piperidine-4-carboxylic acidYield 79.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
85 °C

Procedure

1-(Morpholine-4-sulfonyl)-piperidine-4-carboxylic acid ethyl ester (1.9 g) dissolved in methanol (80 ml) was treated at RT with 2M NaOH (15.5 ml) and the mixture was then heated at 85° C. for 12 h. The solvent was then evaporated off, the residue partitioned between methylene chloride and 1N HCL, the layers were separated and the organic layer washed with 2M aqueous KHCO3, dried over Na2SO4 and concentrated in vacuo to give 1-(morpholine-4-sulfonyl)-piperidine-4-carboxylic acid (1.37 g) as a white solid. MS (ESI): 277.08 ([M-H]−).

Workup

  1. customThe solvent was then evaporated off
  2. customthe residue partitioned between methylene chloride and 1N HCL
  3. customthe layers were separated
  4. washthe organic layer washed with 2M aqueous KHCO3
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3ec7bd2d5457490db0cd26bd40e48906
Source dataset
uspto-grants-2012_09
Patent number
US08258158B2

Reaction notes

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