4-Piperidinecarboxylic acid → 1-Carbobenzoxy-4-piperidinecarboxylic Acid

HRID 862733Notes

Reaction equation

HRID 862733 reaction equation
[NH:1]1[CH2:9][CH2:8][CH:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2]1.Cl[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]>C(=O)([O-])[O-].[Na+].[Na+]>[CH2:14]([O:13][C:11]([N:1]1[CH2:9][CH2:8][CH:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2]1)=[O:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 37734-Piperidinecarboxylic acidHCID 10387Benzyl chloroformate

Product 1

HCID 7364891-Carbobenzoxy-4-piperidinecarboxylic Acid

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

A solution of isonipecotic acid (5.0 g, 38.72 mmol) in 10% aqueous sodium carbonate (100 mL) was cooled to 0° C. and treated with benzyl chloroformate (7.93 g, 46.75 mmol). The resulting biphasic mixture was allowed to warm to room temperature over 2 h, at which time it became homogeneous. The mixture was washed with ether (2×50 mL), then was acidified to pH~2 by addition of concentrated hydrochloric acid. The aqueous solution was extracted with ether (2×100 mL). The organic extracts were washed with brine (50 mL), combined, dried (Na2 SO4), filtered and evaporated to afford the product as a clear oil which slowly crystallized on standing (9.64 g, 36.6 mmol, 95%).

Workup

  1. washThe mixture was washed with ether (2×50 mL)
  2. additionwas acidified to pH~2 by addition of concentrated hydrochloric acid
  3. extractionThe aqueous solution was extracted with ether (2×100 mL)
  4. washThe organic extracts were washed with brine (50 mL)
  5. customdried (Na2 SO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-8e3f1d4cb58f4e89b273a46a97a256dc
Source dataset
uspto-grants-1998_02
Patent number
US05719166

Reaction notes

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