Sulfuric Acid → 4-Phenylpiperidine-4-carboxylic acid, compound with toluene-p-sulphonic acid

HRID 1815517Notes

Reaction equation

HRID 1815517 reaction equation
Cl.[C:2]([C:4]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)#N.[OH-:16].[Na+].[OH:18]S(O)(=O)=O>O>[C:10]1([C:4]2([C:2]([OH:18])=[O:16])[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 30849734-Phenylpiperidine-4-carbonitrile hydrochloride

Product 1

HCID 192594-Phenylpiperidine-4-carboxylic acid, compound with toluene-p-sulphonic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Cyano-4-phenylpiperidine hydrochloride (2.0 g, 0.11 mol) was dissolved in 8 mL of conc. H2SO4 and 4mL of H2O, then the solution was heated at reflux for 4 hours. The solution was cooled and then NaOH was added to precipitate a white solid. The solid was collected, then dissolved in methanol, and the solution was filtered and concentrated to obtain a white solid. This dried solid was used without purification for Example 385B.

Workup

  1. temperatureat reflux for 4 hours
  2. temperatureThe solution was cooled
  3. customto precipitate a white solid
  4. customThe solid was collected
  5. dissolutiondissolved in methanol
  6. filtrationthe solution was filtered
  7. concentrationconcentrated
  8. customto obtain a white solid
  9. customThis dried solid was used without purification for Example 385B

Sources & evidence

ORD record
ord-fc6e5252ac9a4ee1bd3d771fb2889bbe
Source dataset
uspto-grants-2005_04
Patent number
US06878700B1

Reaction notes

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