p-Toluenesulfonic acid monohydrate → 4-Methoxycarbonyl-4-phenylpiperidine p-toluenesulfonate

HRID 362715Notes

Reaction equation

HRID 362715 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:13]1(C)C=CC(S(O)(=O)=O)=CC=1.[C:24]([C:27]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)([OH:26])=[O:25]>CO>[C:2]1([CH3:12])[CH:3]=[CH:4][C:5]([S:8]([OH:11])(=[O:9])=[O:10])=[CH:6][CH:7]=1.[CH3:13][O:25][C:24]([C:27]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]1)=[O:26]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 27236574-Piperidinecarboxylic acid, 4-phenyl-, 4-methylbenzenesulfonate (1:1)

Product 1

HCID 216995184-Methoxycarbonyl-4-phenylpiperidine p-toluenesulfonateYield 453.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 g of p-toluenesulfonic acid monohydrate is added to a solution of 10 g of 4-carboxy-4-phenylpiperidine p-toluenesulfonate in 300 ml of MeOH and the reaction mixture is refluxed for 3 days. It is concentrated under vacuum, the residue is taken up with acetone, and ether is added until precipitation occurs. 9.34 g of the expected product are obtained after wringing of the precipitate formed.

Workup

  1. temperaturethe reaction mixture is refluxed for 3 days
  2. concentrationIt is concentrated under vacuum
  3. additionis added until precipitation

Sources & evidence

ORD record
ord-2381d59a39d84887840dbd04ed733abe
Source dataset
uspto-grants-1999_02
Patent number
US05869663

Reaction notes

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