Hydrochloric Acid → 1-Carbobenzoxy-4-piperidinecarboxylic Acid

HRID 456580Notes

Reaction equation

HRID 456580 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1.[OH-].[Na+].Cl[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].Cl>O1CCOCC1>[CH2:16]([O:15][C:13]([N:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1)=[O:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 37734-Piperidinecarboxylic acidHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide

Product 1

HCID 7364891-Carbobenzoxy-4-piperidinecarboxylic AcidYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of piperidine-4-carboxylic acid (4.7 g, 36 mmol) in 0.5M aqueous sodium hydroxide (160 ml, 80 mmol) and dioxan (50 ml) was treated with benzyl chloroformate (4.3 ml, 5.13 g, 30 mmol). After 1 hour the mixture was acidified with 5M aqueous hydrochloric acid and extracted twice with ethyl acetate. The combined organic extracts were washed with water and brine, then dried and evaporated affording an oil (7.9 g, 100%).

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organic extracts were washed with water and brine
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-c978c8137b8649a6be7682cd4f7ea6e9
Source dataset
uspto-grants-2007_03
Patent number
US07186730B2

Reaction notes

Loading…