Hydrochloric Acid → 2-Phenyl-2-(piperidin-1-yl)acetic acid hydrochloride

HRID 404613Notes

Reaction equation

HRID 404613 reaction equation
[C:1]1([CH:7]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:8]([O:10]CC)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:19]>O1CCOCC1>[ClH:19].[C:1]1([CH:7]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:8]([OH:10])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 202135Ethyl alpha-phenyl-1-piperidineacetate

Product 1

HCID 161894372-Phenyl-2-(piperidin-1-yl)acetic acid hydrochlorideYield 86%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethyl 2-phenyl-2-(piperidin-1-yl)acetate (985 mg, 3.98 mmol) was dissolved in dioxane (33 ml) and 37% HCl (10 ml) was slowly added. The reaction was refluxed for 48 hours and then it was evaporated under reduced pressure. The residue was triturated with acetonitrile (15 ml) and the solid was collected by filtration to obtain 2-phenyl-2-(piperidin-1-yl)acetic acid hydrochloride (876 mg, 86% yield) as a off-white solid. 1H NMR (300 MHz, DMSO-d6) ppm 10.57 (br. s., 1H), 7.33-7.67 (m, 5H), 5.27 (s, 1H), 2.84-3.21 (m, 4H), 1.64-1.98 (m, 4H), 1.31-1.64 (m, 2H)

Workup

  1. temperatureThe reaction was refluxed for 48 hours
  2. customit was evaporated under reduced pressure
  3. customThe residue was triturated with acetonitrile (15 ml)
  4. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-b8c7444f112e40f896e6777959667567
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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