Hydrochloric Acid → 3-Methylsulfonyl-5-nitro-4-piperidinobenzoic acid

HRID 399793Notes

Reaction equation

HRID 399793 reaction equation
Cl[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[S:14]([CH3:17])(=[O:16])=[O:15].[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.C(OCC)(=O)C.Cl>O>[CH3:17][S:14]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:2]=1[N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[C:6]([OH:8])=[O:7])(=[O:16])=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 8857Ethyl AcetateHCID 122745753-Methylsulfonyl-4-chloro-5-nitrobenzoic acid

Product 1

HCID 189454273-Methylsulfonyl-5-nitro-4-piperidinobenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of 4-chloro-3-methylsulfonyl-5-nitrobenzoic acid (5.0 g) and piperidine (25.0 ml) was stirred for 1 hour at ambient temperature. To the mixture was added a mixture of ethyl acetate and water and the mixture was adjusted to pH 1 with conc. hydrochloric acid. The separated organic layer was washed with water and dried over magnesium sulfate. The solvent was removed by concentration and the residue was triturated with a mixture of diisopropyl ether and n-hexane to give 3-methylsulfonyl-5-nitro-4-piperidinobenzoic acid (5.66 g).

Workup

  1. additionTo the mixture was added
  2. washThe separated organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed by concentration
  5. customthe residue was triturated with a mixture of diisopropyl ether and n-hexane

Sources & evidence

ORD record
ord-ce141397dfd14e18870dce3a0633daf1
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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