Piperidine → 2-Nitro-5-(piperidin-1-yl)benzoic acid

HRID 52045

Reaction equation

HRID 52045 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>CC(N(C)C)=O>[N+:11]([C:5]1[CH:4]=[CH:3][C:2]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 172865-Chloro-2-nitrobenzoic acid

Product 1

HCID 144593312-Nitro-5-(piperidin-1-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-chloro-2-nitrobenzoic acid (13.7 g), piperidine (27 ml) and DMA (100 ml) was stirred and heated to 120° C. for 18 hours. The mixture was evaporated. The residue was dissolved in water and the solution was basified to pH10 by the addition of 2N aqueous sodium hydroxide solution. The solution was extracted with ethyl acetate. The aqueous layer was acidified to pH2 by the addition of concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer was dried (MgSO4) and evaporated to give 2-nitro-5-piperidinobenzoic acid (16.25 g), m.p.130°-140° C.

Workup

  1. customThe mixture was evaporated
  2. dissolutionThe residue was dissolved in water
  3. additionthe solution was basified to pH10 by the addition of 2N aqueous sodium hydroxide solution
  4. extractionThe solution was extracted with ethyl acetate
  5. additionThe aqueous layer was acidified to pH2 by the addition of concentrated hydrochloric acid
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic layer was dried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-e548eecaff784fc8846e4a93534b5491
Source dataset
uspto-grants-1997_04
Patent number
US05616582

Linked notes

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