Hydrochloric Acid → Benzyl 4-Hydroxy-1-piperidinecarboxylate

HRID 2425033Notes

Reaction equation

HRID 2425033 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[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14][CH2:13]1.[OH-].[Na+].Cl>O.O1CCOCC1>[CH2:5]([O:4][C:2]([N:12]1[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14][CH2:13]1)=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 79341Piperidin-4-ol

Product 1

HCID 2794620Benzyl 4-Hydroxy-1-piperidinecarboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Benzyl chloroformate (8.55 mL; 60 mmol) was added drop wise over a period of 30 min to a well stirred chilled mixture of piperidin-4-ol (5 g; 49.44 mmol), 1N aqueous NaOH (60 mL; 60 mmol) and dioxane (60 mL). The mixture was stirred for 30 min. at room temperature, treated with water, acidified with conc. HCl to pH 2 and extracted with EtOAc. The EtOAc layer was washed with water, brine, dried (Na2SO4), concentrated and purified using flash chromatography (silica gel, 50% CH2Cl2 in PE 60-80° C., 10% CH3CN+2% MeOH in chloroform). Yield, 12.5 g (99%), oil; MS (CI): 236 (M++1). 218, 192, 174, 91.

Workup

  1. temperaturechilled
  2. stirringThe mixture was stirred for 30 min. at room temperature
  3. extractionextracted with EtOAc
  4. washThe EtOAc layer was washed with water, brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. custompurified
  8. customflash chromatography (silica gel, 50% CH2Cl2 in PE 60-80° C., 10% CH3CN+2% MeOH in chloroform)
  9. customYield

Sources & evidence

ORD record
ord-32a01179d315408cb488d2c883c6ebf4
Source dataset
uspto-grants-2011_06
Patent number
US07964628B2

Reaction notes

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