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

HRID 2093087Notes

Reaction equation

HRID 2093087 reaction equation
CN([CH:4]=[O:5])C.O=P(Cl)(Cl)[Cl:8].O=[C:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]1>>[Cl:8][C:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][C:13]=1[CH:4]=[O:5]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 34767Ethyl 4-oxo-1-piperidinecarboxylate

Product 1

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

Procedure

A solution of DMF (2.5 eq) and POCl3 (1.5 eq.) at 0° C. was stirred for 15 min. To that ethyl 4-oxopiperidine-1-carboxylate (1.0 eq) obtained from step I was added at 40° C. and reaction was continued at room temperature for 2 h Reaction was quenched with water and extracted with ethyl acetate, organic layer was separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude product, which, on purification by column chromatography afforded the desired ethyl 4-chloro-5-formyl-3,6-dihydropyridine-1(2H)-carboxylate.

Workup

  1. customreaction
  2. customReaction
  3. customwas quenched with water
  4. extractionextracted with ethyl acetate, organic layer
  5. customwas separated
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto afford crude product, which
  9. customon purification by column chromatography

Sources & evidence

ORD record
ord-8c2f3497404f480c839405df9ecb521d
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

Loading…