Water → HCID 12784661, compound

HRID 1245117Notes

Reaction equation

HRID 1245117 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH2:15][CH:14]([CH3:16])[CH2:13][CH:12]([CH3:17])[CH2:11]2)=C([CH:9]=1)C#N.[OH-].[K+].O.[C:21]([O:24]CC)(=[O:23])[CH3:22]>COCCOCCO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH2:11][CH:12]([CH3:17])[CH2:13][CH:14]([CH3:16])[CH2:15]2)=[C:22]([CH:9]=1)[C:21]([OH:24])=[O:23]

Participants

6

Reactant 4

HCID 962Water2×HCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 21921950HCID 21921950, compound

Product 1

HCID 12784661HCID 12784661, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8134Diethylene Glycol Monomethyl EtherSolvent

Procedure

To a solution of 5-chloro-2-(3,5-dimethyl-piperidin-1-yl)-benzonitrile (1.05 g, 4.220 mmol) in Diethylene glycol monomethyl ether (2.50 mL) was added KOH (0.947 g, 16.883 mmol) and water (0.750 ml). The reaction was heated at 130–135° C. overnight. Upon cooling to rt, water and ethyl acetate was added the organic layer was discarded and the aqueous layer is acidified to pH˜6–7. The aqueous layer was then extracted with ethyl acetate three times. The combined organic layer was washed with water, brine, dried (Na2SO4), and concentrated to give required 5-chloro-2-(3,5-dimethyl-piperidin-1-yl)-benzoic acid (0.850 g, 75%) as an off white solid. LCMS 268(M+1)+.

Workup

  1. temperatureThe reaction was heated at 130–135° C. overnight
  2. extractionThe aqueous layer was then extracted with ethyl acetate three times
  3. washThe combined organic layer was washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a54655f185304b79865e4fa42f1afc4f
Source dataset
uspto-grants-2006_10
Patent number
US07122580B2

Reaction notes

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