Sulfuric Acid → Methyl 4-phenylpiperidine-4-carboxylate

HRID 405932Notes

Reaction equation

HRID 405932 reaction equation
S(=O)(=O)(O)O.[C:6]1(C)C=CC(S(O)(=O)=O)=CC=1.[C:17]1([C:23]2([C:29]([OH:31])=[O:30])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-].[Na+]>CO>[C:17]1([C:23]2([C:29]([O:31][CH3:6])=[O:30])[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 27236574-Piperidinecarboxylic acid, 4-phenyl-, 4-methylbenzenesulfonate (1:1)

Product 1

HCID 545827Methyl 4-phenylpiperidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

270 ml of methanol are taken. 10.6 ml sulphuric acid and 25 g 4-phenyl-4-piperidine-carboxylic acid p-toluenesulphonic acid are added with stirring. The reaction mixture is refluxed for 9 h, cooled and carefully poured onto a mixture of ice water and 10 M NaOH. The precipitated solid is suction filtered, washed with water and dried. 11.2 g (V-15) are obtained as a solid.

Workup

  1. temperatureThe reaction mixture is refluxed for 9 h
  2. temperaturecooled
  3. filtrationfiltered
  4. washwashed with water
  5. customdried
  6. custom11.2 g (V-15) are obtained as a solid

Sources & evidence

ORD record
ord-b57faca746684a8cbc68d2b36159f7e1
Source dataset
uspto-grants-2014_06
Patent number
US08754073B2

Reaction notes

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