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

HRID 1585241Notes

Reaction equation

HRID 1585241 reaction equation
[NH:1]1[CH2:9][CH2:8][CH:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.C1(C)C=CC=CC=1>[CH2:21]([O:20][C:18]([N:1]1[CH2:9][CH2:8][CH:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2]1)=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 37734-Piperidinecarboxylic acidHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformate

Product 1

HCID 7364891-Carbobenzoxy-4-piperidinecarboxylic AcidYield 26.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a slurry of 66.4 g (0.50 mol) of isonipecotic acid, and 145 mL (0.50 mol) of triethylamine in 600 mL of methylene chloride was added a solution of 72 mL (0.50 mol) of benzyl chloroformate in 200 mL of toluene at 10° C. The slurry was allowed to warm to room temperature and after stirring for 17 h was treated with 1 L of a 10% aqueous sodium carbonate solution. The layers were separated, and the aqueous portion was extracted once with ether and then acidified to pH 3. The aqueous portion was then extracted with methylene chloride. The organic extract was washed with brine, dried over MgSO4 and concentrated to give 35.2 g of the title compound as an oil which was used without further purification.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous portion was extracted once with ether
  3. extractionThe aqueous portion was then extracted with methylene chloride
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4df55b4f59694373875b7555752e6b08
Source dataset
uspto-grants-1999_08
Patent number
US05936089

Reaction notes

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