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

HRID 849334Notes

Reaction equation

HRID 849334 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 RiT. The acetone is evaporated under vacum, 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. customThe acetone is evaporated under vacum
  3. additionby adding concentrated aqueous solution of HCl
  4. additionby adding a 2N HCl solution
  5. customThe precipitate formed
  6. washwashed with water

Sources & evidence

ORD record
ord-35f61e6c851b4a0ea1452ff07497c43d
Source dataset
uspto-grants-2000_01
Patent number
US06011154

Reaction notes

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