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

HRID 2388723
Notes
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Reaction equation

HRID 2388723 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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-carboxylate

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
25 °C

Procedure

POCl3 (2.18 g, 23.4 mmol) was added very slowly to 2.7 ml of dry DMF at 0° C. The mixture obtained was stirred at 25° C. for 15 minutes. After the reaction temperature had been reduced again to 0° C., N-ethoxycarbonylpiperidone (11.7 mmol) was added. The reaction mixture obtained was stirred at 25° C. for 3 hours. Thereafter, sodium acetate (7 g) and water (8.5 ml) were added and the mixture was stirred. The reaction mixture was extracted with benzene. The organic phase was washed successively with water, sodium carbonate and saturated sodium chloride solution. After the organic phase had been dried over sodium sulfate, the solvent was removed under reduced pressure. The crude product obtained was employed in the next stage without further purification. The crude yield was 63%.

Workup

  1. customThe mixture obtained
  2. customhad been reduced again to 0° C.
  3. customThe reaction mixture obtained
  4. stirringwas stirred at 25° C. for 3 hours
  5. stirringthe mixture was stirred
  6. extractionThe reaction mixture was extracted with benzene
  7. washThe organic phase was washed successively with water, sodium carbonate and saturated sodium chloride solution
  8. dry with materialAfter the organic phase had been dried over sodium sulfate
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f28757da79014f3db38549961e3af480
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08268814B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes