Sodium Hydroxide → 1-[4-(4-Chlorophenyl)piperazine-1-sulfonyl]piperidine-2-(rs)-carboxylic acid

HRID 609682Notes

Reaction equation

HRID 609682 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]3[C:23]([O:25]C)=[O:24])(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-].[Na+]>CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][N:11]([S:14]([N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]3[C:23]([OH:25])=[O:24])(=[O:15])=[O:16])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22615694Methyl 1-[4-(4-chlorophenyl)piperazine-1-sulfonyl]piperidine-2-(rs)-carboxylate

Product 1

HCID 226157981-[4-(4-Chlorophenyl)piperazine-1-sulfonyl]piperidine-2-(rs)-carboxylic acidYield 79%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of methyl 1-[4-(4-chlorophenyl)piperazine-1-sulfonyl]piperidine-2-(RS)-carboxylate (164 mg, 0.41 mmol), [prepared as described in Example 3] and NaOH (33 mg, 0.82 mmol) in methanol/water (5 ml of 9:1 ratio) was heated at reflux. After 2 h, the reaction mixture was concentrated in vacuo, diluted with water (5 ml) and extracted with diethyl ether. The aqueous phase was acidified to pH 3 with 5% potassium bisulfate solution and the product was extracted into ethyl acetate. The organic phase was washed with brine, dried over MgSO4, and concentrated to yield 1-[4-(4-chlorophenyl)piperazine-1-sulfonyl]piperidine-2-(RS)-carboxylic acid as a foam (125 mg, 79%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. additiondiluted with water (5 ml)
  5. extractionextracted with diethyl ether
  6. extractionthe product was extracted into ethyl acetate
  7. washThe organic phase was washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-40d7f1b2ab83423fa6028e979774ec91
Source dataset
uspto-grants-1999_12
Patent number
US05998412

Reaction notes

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