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

HRID 1601895Notes

Reaction equation

HRID 1601895 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 g 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 2 N 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-9e596b76c480494ba30e0c3763b1f71f
Source dataset
uspto-grants-1999_11
Patent number
US05977359

Reaction notes

Loading…