Hydrochloric Acid → 1-(Benzyloxycarbonyl)-4-phenylpiperidine-4-carboxylic acid

HRID 2111605Notes

Reaction equation

HRID 2111605 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:12]1([C:18]2([C:24]([OH:26])=[O:25])[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[Na+].Cl[C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31].Cl>O.CC(C)=O>[CH2:33]([O:32][C:30]([N:21]1[CH2:20][CH2:19][C:18]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)([C:24]([OH:26])=[O:25])[CH2:23][CH2:22]1)=[O:31])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 27236574-Piperidinecarboxylic acid, 4-phenyl-, 4-methylbenzenesulfonate (1:1)

Product 1

HCID 227417981-(Benzyloxycarbonyl)-4-phenylpiperidine-4-carboxylic acidYield 66.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent3×HCID 962WaterSolvent2×

Conditions

Temperature
5 °C

Procedure

A mixture of 151 g of 4-phenylpiperidine-4-carboxylic acid p-toluenesulfonate and 213 g of aqueous 30% NaOH solution in 500 ml of water is cooled to 5° C. A solution of 68.2 g of benzyl chloroformate in 150 ml of acetone is added dropwise and the mixture is stirred for 6 days while allowing the temperature to return to rt. 150 ml of acetone are added and the reaction mixture is poured onto a mixture of 200 g of concentrated HCl solution, 300 ml of water and 300 ml of acetone precooled on an ice bath. The precipitate formed is filtered off by suction and washed with water and then with ether. 89.7 g of the expected product are obtained.

Workup

  1. customto return to rt
  2. customprecooled on an ice bath
  3. customThe precipitate formed
  4. filtrationis filtered off by suction
  5. washwashed with water

Sources & evidence

ORD record
ord-c540df640e2349d88b1f177aa670bec1
Source dataset
uspto-grants-2009_04
Patent number
US07521449B2

Reaction notes

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