Hydrochloric Acid → 1-Carbobenzoxy-4-piperidinecarboxylic Acid

HRID 557961Notes

Reaction equation

HRID 557961 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[NH:7]1[CH2:12][CH2:11][CH:10]([C:13]([OH:15])=[O:14])[CH2:9][CH2:8]1.Cl[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].Cl>O>[CH2:20]([O:19][C:17]([N:7]1[CH2:12][CH2:11][CH:10]([C:13]([OH:15])=[O:14])[CH2:9][CH2:8]1)=[O:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 37734-Piperidinecarboxylic acidHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformate

Product 1

HCID 7364891-Carbobenzoxy-4-piperidinecarboxylic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium carbonate (1.59 g, 0.0150 mol) was added to a solution of piperidine-4-carboxylic acid (0.970 g, 0.00751 mol) in water (15 mL). After the solid was dissolved, benzyl chloroformate (1.54 g, 0.00901 mol) was added dropwise. The mixture was stirred at rt for 3 h. The mixture was carefully acidified (pH=4) with 2N HCl, and then was extracted with DCM (4×10 mL). The combined organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to give the desired product.

Workup

  1. dissolutionAfter the solid was dissolved
  2. extractionwas extracted with DCM (4×10 mL)
  3. dry with materialThe combined organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-96fb5919551a4290b9395be4c27b7de8
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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