Dimethylformamide → Ethyl 4-chloro-3-formyl-5,6-dihydro-2H-pyridine-1-carboxylate

HRID 2388678Notes

Reaction equation

HRID 2388678 reaction equation
O=P(Cl)(Cl)[Cl:3].CN([CH:9]=[O:10])C.[CH2:11]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C:17]1=O)=[O:15])[CH3:12].C([O-])(=O)C.[Na+]>O>[Cl:3][C:19]1[CH2:20][CH2:21][N:16]([C:14]([O:13][CH2:11][CH3:12])=[O:15])[CH2:17][C:18]=1[CH:9]=[O:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 13303317Ethyl 2-oxopiperidine-1-carboxylate

Product 1

HCID 3024580Ethyl 4-chloro-3-formyl-5,6-dihydro-2H-pyridine-1-carboxylateYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

POCl3 (2.18 g, 23.4 mmol) was added very slowly to dry DMF (2.7 ml) at 0° C. and the resulting mixture was stirred at 25° C. for 15 min. The reaction mixture was again cooled to 0° C., and N-ethoxycarbonyl piperidone (11.7 mmol) was added. The resulting reaction mixture was stirred at 25° C. for 3 h. It was then stirred with sodium acetate (7 g) and water (8.5 ml) and extracted with benzene. The organic layer was successively washed with water, sodium hydrogencarbonate an brine and was finally dried over sodium sulfate. Evaporation of the organic layer under reduced pressure gave the crude product, which was used directly in the next step without further purification. Yield: 63%.

Workup

  1. temperatureThe reaction mixture was again cooled to 0° C.
  2. customThe resulting reaction mixture
  3. stirringwas stirred at 25° C. for 3 h
  4. extractionextracted with benzene
  5. washThe organic layer was successively washed with water, sodium hydrogencarbonate an brine
  6. dry with materialwas finally dried over sodium sulfate
  7. customEvaporation of the organic layer under reduced pressure

Sources & evidence

ORD record
ord-05765538068c4fd39faea947c7509f6a
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

Loading…