Dimethylformamide → 1-Methylpiperidine-4-carbonyl chloride

HRID 1963722Notes

Reaction equation

HRID 1963722 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=O)[CH2:4][CH2:3]1.CN(C)C=O.C(Cl)(=O)C([Cl:19])=O>C(Cl)Cl>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]([Cl:19])=[O:10])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 27369391-Methylpiperidine-4-carboxylic acid

Product 1

HCID 4365031-Methylpiperidine-4-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

A flask was flame dried and placed under a nitrogen atmosphere. 1-methylpiperidine-4-carboxylic acid (1 eq) in anhydrous methylene chloride added to flask and cooled to 20° C. in a water bath. Dimethylformamide added, then oxalyl chloride (1.4 eq) in methylene chloride. Reaction refluxed for 2 hours, brought to room temperature, concentrated and azeotroped with toluene to yield 1-methylpiperidine-4-carbonyl chloride as a light yellow fluffy solid. MS: MH+=162.

Workup

  1. temperatureA flask was flame
  2. customdried
  3. customReaction
  4. temperaturerefluxed for 2 hours
  5. custombrought to room temperature
  6. concentrationconcentrated
  7. customazeotroped with toluene

Sources & evidence

ORD record
ord-48962e61c2914927a0358ba0984cff14
Source dataset
uspto-grants-2013_04
Patent number
US08415382B2

Reaction notes

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