4-Piperidinecarboxylic acid, 4-phenyl-, 4-methylbenzenesulfonate (1:1) → 1-Benzyl-4-phenylpiperidine-4-carboxylic acid

HRID 1957053Notes

Reaction equation

HRID 1957053 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4](S(O)(=O)=O)=[CH:3][CH:2]=1.[C:12]([C:15]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)([OH:14])=[O:13]>O.CC(C)=O>[CH2:11]([N:18]1[CH2:19][CH2:20][C:15]([C:12]([OH:14])=[O:13])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][CH2:17]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 27236574-Piperidinecarboxylic acid, 4-phenyl-, 4-methylbenzenesulfonate (1:1)

Product 1

HCID 965761-Benzyl-4-phenylpiperidine-4-carboxylic acidYield 89.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

106 ml of a 30% NAOH solution is added to a suspension of 100 g of 4-carboxy-4-phenylpiperidine p-toluenesulfonate in 600 ml of water, then the thus obtained solution is cooled to 5° C., a solution of 47.6 g of bromide benzyl in 100 ml of acetone is added dropwise and left under stirring for 1 hour while the temperature being allowed to rise to RT. The acetone is evaporated under vacuum, and the pH of the remaining aqueous phase is brought to 9.5 by adding concentrated aqueous solution of HCl, then the pH is adjusted to 8.5 by adding a 2N HCl solution. The precipitate formed is wrung and washed with water and then with acetone to give 70 g of the expected compound, M.p.=286° C.

Workup

  1. waitleft
  2. customto rise to RT
  3. customThe acetone is evaporated under vacuum
  4. additionby adding concentrated aqueous solution of HCl
  5. additionby adding a 2N HCl solution
  6. customThe precipitate formed
  7. washwashed with water

Sources & evidence

ORD record
ord-e7529bd2bb9a4c2bac585531b71fe84f
Source dataset
uspto-grants-1998_07
Patent number
US05780466

Reaction notes

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