Oxalyl chloride → benzyl 3-(chlorocarbonyl)tetrahydro-1(2H)-pyridinecarboxylate

HRID 17865

Reaction equation

HRID 17865 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]([OH:19])=O)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:23])=O>CN(C)C=O.C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]([Cl:23])=[O:19])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 2343391-((Benzyloxy)carbonyl)piperidine-3-carboxylic acid

Product 1

HCID 2776575benzyl 3-(chlorocarbonyl)tetrahydro-1(2H)-pyridinecarboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To an ice cooled methylene chloride solution of 1-[(Benzyloxy)carbonyl]piperidine-3-carboxylic acid (512 mg, 1.95 mmol) under nitrogen was added oxalyl chloride (0.185 mL, 1.95 mmol) and a few drops N,N-dimethylformamide. The reaction flask was warmed slowly to room temperature and after 2 hours the solvent was removed in vacuo. Toluene was added and removed in vacuo (2×) to give the title compound.

Workup

  1. customwas removed in vacuo
  2. additionToluene was added
  3. customremoved in vacuo (2×)

Sources & evidence

ORD record
ord-41058c22e6b04ecb9835b0c445873296
Source dataset
uspto-grants-2010_06
Patent number
US07741322B2

Linked notes

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