Benzyl Alcohol → 4-Piperidinecarboxylic acid, phenylmethyl ester

HRID 1177873Notes

Reaction equation

HRID 1177873 reaction equation
S(Cl)(Cl)=O.[NH:5]1[CH2:10][CH2:9][CH:8]([C:11]([OH:13])=[O:12])[CH2:7][CH2:6]1.[CH2:14](O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH2:14]([O:12][C:11]([CH:8]1[CH2:9][CH2:10][NH:5][CH2:6][CH2:7]1)=[O:13])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 244Benzyl AlcoholHCID 37734-Piperidinecarboxylic acidHCID 24386Thionyl Chloride

Product 1

HCID 114133364-Piperidinecarboxylic acid, phenylmethyl esterYield 97.25%

Procedure

Thionyl chloride (5.42 g, 46 mmol) was added to a cold (0-4° C.) stirred solution piperidine-4-carboxylic acid (5 g, 38.7 mmol) in benzyl alcohol (150 mL) and stirring was continued overnight. Benzyl alcohol was removed by stirring with hexane, ether and decanting the solvent, dried to afford 8.26 g (97.25% yield) of piperidine-4-carboxylic acid benzyl ester. LCMS Purity: 94.8%.

Workup

  1. customBenzyl alcohol was removed
  2. stirringby stirring with hexane, ether
  3. customdecanting the solvent
  4. customdried

Sources & evidence

ORD record
ord-9e2ad0e6c14d4ec79ca2c63acf10558a
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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