Dimethylformamide → 1-BOC-4-CHLORO-5-FORMYL-3,6-DIHYDRO-2H-PYRIDINE

HRID 629629Notes

Reaction equation

HRID 629629 reaction equation
CN(C)[CH:3]=[O:4].P(Cl)(Cl)([Cl:8])=O.O=[C:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1.C([O-])(=O)C.[Na+]>ClCCl>[Cl:8][C:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][C:13]=1[CH:3]=[O:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 118450841-BOC-4-CHLORO-5-FORMYL-3,6-DIHYDRO-2H-PYRIDINE

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To N,N-dimethylformamide (3.87 mL) at 0° C., phosphorus oxychloride (3.73 mL) was added dropwise, maintaining the temperature below 5° C. The resulting mixture was diluted with dichloromethane (15 mL) and stirred at room temperature for 1.5 hours. The reaction was then cooled in an ice bath. tert-Butyl 4-oxopiperidine-1-carboxylate (4.98 g) was added as a solution in dichloromethane (20 mL) and the reaction was stirred at room temperature for 1 hour. The reaction mixture was poured over ice and solid sodium acetate, stirred for 15 minutes, and extracted with dichloromethane. The extracts were washed thoroughly with water and with brine, dried over MgSO4, filtered, and concentrated to obtain the title compound.

Workup

  1. temperaturemaintaining the temperature below 5° C
  2. temperatureThe reaction was then cooled in an ice bath
  3. stirringthe reaction was stirred at room temperature for 1 hour
  4. stirringstirred for 15 minutes
  5. extractionextracted with dichloromethane
  6. washThe extracts were washed thoroughly with water and with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-f83ac12d0e524c08bc03c52597a61f96
Source dataset
uspto-grants-2016_04
Patent number
US09315488B2

Reaction notes

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