Hydrochloric Acid → 1-(4-Fluorobenzoyl)piperidine-3-carboxylic acid

HRID 1172728Notes

Reaction equation

HRID 1172728 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12](=[O:20])[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH2:7]1)=[O:5])C.Cl.C(Cl)Cl>CCO.[OH-].[Na+]>[F:19][C:16]1[CH:15]=[CH:14][C:13]([C:12]([N:8]2[CH2:9][CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7]2)=[O:20])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 2905457Ethyl 1-(4-fluorobenzoyl)piperidine-3-carboxylate

Product 1

HCID 47136431-(4-Fluorobenzoyl)piperidine-3-carboxylic acidYield 101.8%

Reagents, catalysts & solvents 1

HCID 23692425Sodium hydroxide ethanolSolvent

Procedure

1-(4-Fluoro-benzoyl)-piperidine-3-carboxylic acid ethyl ester (1.15 g, 4.42 mmol) was added in a mixture of EtOH/NaOH 3N:1/1 (8 ml) and the resulting heterogeneous solution was stirred at R.T for 1 h. Fuming HCl was added to the mixture until pH=1. The solution was poured with DCM. The organic layer was separated and the aqueous phase was extracted twice with DCM. The combined organic phase was washed twice with water. The solution was dried over Na2SO4, filtered and concentrated to afford 1.13 g (100%) of 1-(4-Fluoro-benzoyl)-piperidine-3-carboxylic acid as an orange oil which can be used without further purification.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous phase was extracted twice with DCM
  3. washThe combined organic phase was washed twice with water
  4. dry with materialThe solution was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fcdfc476b5d447ab8887f45635aa8690
Source dataset
uspto-grants-2010_11
Patent number
US07834035B2

Reaction notes

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