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

HRID 376262Notes

Reaction equation

HRID 376262 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.C1([C:18]2([C:24]([OH:26])=[O:25])[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)C=CC=CC=1.ClC(OCC1C2CC3C(=CC=CC=3)C=2C=CC=1)=O>C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1.O>[NH:21]1[CH2:22][CH2:23][CH:18]([C:24]([OH:26])=[O:25])[CH2:19][CH2:20]1

Participants

6

Reactant 2

HCID 27236574-Piperidinecarboxylic acid, 4-phenyl-, 4-methylbenzenesulfonate (1:1)HCID 14261773Fluorenylmethyl chloroformate

Product 1

HCID 37734-Piperidinecarboxylic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a suspension of 3.77 g (10 mmol) of 4-phenyl-4-piperidine-carboxylic acid p-toluenesulfonic acid salt (commercially available) in 31 ml of 10% Na2CO3 and 15 ml of dioxane was added at 0° C. a solution of 2.58 g (10 mmol) of fluorenylmethyl chloroformate in 20 ml of dioxane dropwise. The reacion mixture was stirred for 3 hours, diluted with 50 ml of water and extracted with EtOAc (3×20 ml). The aqueous phase was acidified with conc HCl while stirring vigorously in an ice bath. The resulting solid was collected by filtration, washed with water and dried in vacuo to provide the title compound. 1H-NMR (CDCl3, 300 MHz): 1.85 (bm, 2H); 2.50 (bm, 2H); 3.15 (bm, 2H); 3.80-4.10 (m, 2H); 4.25 (t, 1H); 4.5 (d, 2H); 7.25-7.50 (m, 9H); 7.59 (d, 2H); 7.80 (d, 2H).

Workup

  1. extractionextracted with EtOAc (3×20 ml)
  2. stirringwhile stirring vigorously in an ice bath
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-96fba9bcf3d84eef9243e3097fff444e
Source dataset
uspto-grants-2000_02
Patent number
US06020347

Reaction notes

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