Water → 1-(Benzyloxycarbonyl)-4-phenylpiperidine-4-carboxylic acid

HRID 1957045Notes

Reaction equation

HRID 1957045 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=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].[OH-].[Na+].O.Cl[C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32]>CC(C)=O>[CH2:34]([O:33][C:31]([N:18]1[CH2:17][CH2:16][C:15]([C:12]([OH:14])=[O:13])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:20][CH2:19]1)=[O:32])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 27236574-Piperidinecarboxylic acid, 4-phenyl-, 4-methylbenzenesulfonate (1:1)

Product 1

HCID 227417981-(Benzyloxycarbonyl)-4-phenylpiperidine-4-carboxylic acidYield 90.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 37.7 g of 4-carboxy-4-phenylpiperidine p-toluenesulfonate, 53.3 g of 30% aqueous NaOH solution and 250 ml of water is cooled to 5° C. A solution of 18 g of benzyl chloroformate in 60 ml of acetone is added rapidly at 5° C. and the reaction mixture is stirred overnight while the temperature is allowed to rise to RT. It is washed twice with ether and, after decantation, the aqueous phase is acidified to pH 1 by the addition of concentrated HCl and then 2N HCl. The precipitate formed is wrung, dried, taken up with ether and wrung again to give 30.6 g of the expected product. M.p.=142°-144° C.

Workup

  1. customto rise to RT
  2. washIt is washed twice with ether
  3. additionafter decantation, the aqueous phase is acidified to pH 1 by the addition of concentrated HCl
  4. customThe precipitate formed
  5. customdried

Sources & evidence

ORD record
ord-7acb641f36364716929eecb29d236c94
Source dataset
uspto-grants-1998_07
Patent number
US05780466

Reaction notes

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