Water → 4-(4-Methyl-1-piperidinyl)benzoic acid

HRID 1354775Notes

Reaction equation

HRID 1354775 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#N)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[OH-:16].[K+].[OH2:18]>C(O)CO>[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]([OH:18])=[O:16])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 962Water2×HCID 14797Potassium HydroxideHCID 31520804-(4-Methyl-piperidin-1-yl)-benzonitrile

Product 1

HCID 6548094-(4-Methyl-1-piperidinyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

4-(4-Methylpiperidin1-yl)benzonitrile (1.2 g) was heated to reflux with potassium hydroxide (0.7 g) in water (2 ml) and ethylene glycol (8 ml) for 3 hours. The mixture was diluted with water, washed with ethyl acetate and acidified with 2N hydrochloric acid. The precipitated product was filtered off with suction, dissolved in dichloromethane, dried over sodium sulfate, concentrated and crystallized from diethyl ether. This resulted in the product with the molecular weight of 219.29 (C13H17NO2); MS(ESI): 220 (M+H+).

Workup

  1. washwashed with ethyl acetate
  2. filtrationThe precipitated product was filtered off with suction
  3. dissolutiondissolved in dichloromethane
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customcrystallized from diethyl ether
  7. customThis resulted in the product with the molecular weight of 219.29 (C13H17NO2)

Sources & evidence

ORD record
ord-09bf709467f24213b3fa62997fb2af80
Source dataset
uspto-grants-2007_05
Patent number
US07223788B2

Reaction notes

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