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

HRID 1815522Notes

Reaction equation

HRID 1815522 reaction equation
[NH:1]1[CH2:9][CH2:8][CH2:7][CH:3]([C:4]([OH:6])=[O:5])[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>C(OCC)C>[CH2:12]([O:19][C:20]([N:1]1[CH2:9][CH2:8][CH2:7][CH:3]([C:4]([OH:6])=[O:5])[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 Hydroxide2×

Product 1

HCID 2343391-((Benzyloxy)carbonyl)piperidine-3-carboxylic acidYield 113%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of nipecotic acid 10 g, 63.6 mmol) in 1 N NaOH (2.5 g in 64 mL water, 63.6 mmol) at 0° C. was alternately added benzyloxycarbonyl chloride (10.9 mL, 76.5 mmol) in diethyl ether (50 mL) and 1 N NaOH (5 g in 128 mL water, 127.2 mmol) in five portions. The reaction mixture was stirred at 0° C. for 2 hours, and at ambient temperature for 24 hours. Then this was made acidic with 10% HCl and the solid formed was filtered and dried (vacuum oven, 45° C.) to obtain the title compound (18.9 g, 113%). MS (ESI) m/e 264 (M+H)+.

Workup

  1. customat 0° C.
  2. waitat ambient temperature for 24 hours
  3. customthe solid formed
  4. filtrationwas filtered
  5. customdried (vacuum oven, 45° C.)

Sources & evidence

ORD record
ord-ad7a19072f7847f3ae361b1d200ae460
Source dataset
uspto-grants-2005_04
Patent number
US06878700B1

Reaction notes

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