HCID 178492988, compound → 5-Chloro-2-methoxy-4-(piperidin-1-yl)-phenylacetic acid

HRID 637669Notes

Reaction equation

HRID 637669 reaction equation
N1(C(N)=O)CC[O:4]CC1.[Cl:10][C:11]1[C:12]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:13][C:14]([O:21][CH3:22])=[C:15]([CH2:17][C:18]([OH:20])=S)[CH:16]=1>C(O)(=O)C.Cl.O>[Cl:10][C:11]1[C:12]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:13][C:14]([O:21][CH3:22])=[C:15]([CH2:17][C:18]([OH:4])=[O:20])[CH:16]=1

Participants

5

Reactant 1

HCID 178492988HCID 178492988, compound

Product 1

HCID 541834705-Chloro-2-methoxy-4-(piperidin-1-yl)-phenylacetic acid

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution of 11.07 g (30 mmole) of 5-chloro-2-methoxy-4-(piperidin-1-yl)-phenylthioacetic acid morpholinamide in 120 ml of glacial acetic acid and 30 ml of concentrated hydrochloric acid is boiled under reflux for 22 hours. The reaction mixture is cooled, diluted with water and extracted with methylene chloride. The combined methylene chloride phases are washed with water, dried over sodium sulphate and concentrated by evaporation in a vacuum rotary evaporator. Chromatography over silica gel with chloroform/methanol (19:1) yields 5-chloro-2-methoxy-4-(piperidin-1-yl)-phenylacetic acid which after recrystallisation with methylene chloride/hexane melts at 120°-122°.

Workup

  1. temperatureunder reflux for 22 hours
  2. temperatureThe reaction mixture is cooled
  3. extractionextracted with methylene chloride
  4. washThe combined methylene chloride phases are washed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated by evaporation in a vacuum rotary evaporator

Sources & evidence

ORD record
ord-cb609007ce9a4a34bf52b53e75893506
Source dataset
uspto-grants-1985_12
Patent number
US04558043

Reaction notes

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