Hydrochloric Acid → 1-((Benzyloxy)carbonyl)piperidine-3-carboxylic acid

HRID 415262Notes

Reaction equation

HRID 415262 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]([OH:9])=[O:8])[CH2:2]1.[OH-].[Na+].[CH2:12]([O:19][C:20](Cl)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>O>[CH2:12]([O:19][C:20]([N:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]([OH:9])=[O:8])[CH2:2]1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4498Nipecotic AcidHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide

Product 1

HCID 2343391-((Benzyloxy)carbonyl)piperidine-3-carboxylic acidYield 83.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of piperidine-3-carboxylic acid (1.3 g, 10 mmol) in water (20 mL) was added sodium hydroxide (1.6 g, 40 mmol). Then benzyloxycarbonyl chloride (2.02 g, 12 mmol) was added dropwise at 0° C. The mixture was stirred at 0° C. for 2 h. The resulting mixture was treated with 5N hydrochloric acid to pH=6 and extracted with ethyl acetate, the solvent was removed under reduced pressure and dried in vacuum. 2.2 g of solid of 1-(benzyloxycarbonyl)piperidine-3-carboxylic acid was obtained. LC-MS (ESI) m/z: 264 (M+1)+.

Workup

  1. extractionextracted with ethyl acetate
  2. customthe solvent was removed under reduced pressure
  3. customdried in vacuum

Sources & evidence

ORD record
ord-d86f88a213c844b885da242cb66e1d5b
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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