Hydrochloric Acid → 1-Carbobenzoxy-4-piperidinecarboxylic Acid

HRID 1373259Notes

Reaction equation

HRID 1373259 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].[NH:12]1[CH2:20][CH2:19][CH:15]([C:16]([OH:18])=[O:17])[CH2:14][CH2:13]1.C(=O)([O-])O.[Na+].Cl>C(OCC)C>[CH2:5]([O:4][C:2]([N:12]1[CH2:20][CH2:19][CH:15]([C:16]([OH:18])=[O:17])[CH2:14][CH2:13]1)=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 37734-Piperidinecarboxylic acidHCID 10387Benzyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 7364891-Carbobenzoxy-4-piperidinecarboxylic AcidYield 72%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A diethyl ether (50 ml) solution of benzyl chloroformate (36 g, 0.21 mols) was dropwise added to an aqueous solution (200 ml) of isonipecotic acid (25 g, 0.19 mols) and sodium hydrogencarbonate (49 g, 0.58 mols) with stirring at room temperature. After the addition, this was further stirred at room temperature for 15 hours. The reaction mixture was acidified with concentrated hydrochloric acid added thereto, and then extracted with ethyl acetate. The extract was washed with brine, then dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was crystallized from isopropyl ether/hexane, and taken out through filtration. A colorless crystal of N-benzyloxycarbonylisonipecotic acid (36 g, 71%) was obtained.

Workup

  1. additionAfter the addition
  2. stirringthis was further stirred at room temperature for 15 hours
  3. additionadded
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was crystallized from isopropyl ether/hexane
  9. filtrationtaken out through filtration

Sources & evidence

ORD record
ord-27df418a1e3143f6a4cb935129378810
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

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