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

HRID 730194Notes

Reaction equation

HRID 730194 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].CC1C=CC(S(O)(=O)=O)=CC=1.[C:23]1([C:29]2([C:35]([OH:37])=[O:36])[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.ClCCl.Cl>[OH-].[Na+]>[CH2:5]([O:4][C:2]([N:32]1[CH2:31][CH2:30][C:29]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)([C:35]([OH:37])=[O:36])[CH2:34][CH2:33]1)=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 10387Benzyl chloroformateHCID 27236574-Piperidinecarboxylic acid, 4-phenyl-, 4-methylbenzenesulfonate (1:1)

Product 1

HCID 227417981-(Benzyloxycarbonyl)-4-phenylpiperidine-4-carboxylic acidYield 94.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Benzyl chloroformate (4.75 mL, 33.1 mmol) was added dropwise to a solution of 4-phenyl-4-piperidinecarboxylic acid p-methylbenzenesulfonate (10.0 g, 26.5 mmol) in 1M sodium hydroxide (200 mL)/dichloromethane (100 mL). After 2 hours the reaction mixture was made acidic with 1M hydrochloric acid (pH=3), the organic layer was separated and the aqueous layer extracted with ethyl acetate (3×100 mL). The organic layers were collected, concentrated and crude product washed with water (3×50 mL) to give 8.52 g of 4-phenyl-piperidine-1,4-dicarboxylic acid monobenzyl ester. LRMS m/z 340.2 (M+H)+.

Workup

  1. customthe organic layer was separated
  2. extractionthe aqueous layer extracted with ethyl acetate (3×100 mL)
  3. customThe organic layers were collected
  4. concentrationconcentrated
  5. washcrude product washed with water (3×50 mL)

Sources & evidence

ORD record
ord-e88e268039e84aa49a4c7bbc4616380b
Source dataset
uspto-grants-2009_09
Patent number
US07582654B2

Reaction notes

Loading…