Sodium Acetate → HCID 22727172, compound

HRID 2086263Notes

Reaction equation

HRID 2086263 reaction equation
O.Cl.[NH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=O.Cl[C:11]1[CH:16]=[CH:15][N:14]=[C:13]([CH3:17])[CH:12]=1.C([O-])(=[O:20])C.[Na+]>C(O)(=O)C>[CH3:17][C:13]1[CH:12]=[C:11]([N:3]2[CH2:8][CH2:7][C:6](=[O:20])[CH2:5][CH2:4]2)[CH:16]=[CH:15][N:14]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 5813924-Chloro-2-methylpyridineHCID 22021827Piperidone monohydrate hydrochloride

Product 1

HCID 22727172HCID 22727172, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of piperidone hydrochloride hydrate (68.98 g), 4-chloro-2-picolin (47.7 g) and sodium acetate (36.8 g) in acetic acid (500 ml) was refluxed for 15 hours and then the reaction mixture was concentrated, and the resultant residue was dissolved in water, combined with potassium hydroxide to make alkaline, and then extracted with dichloromethane, dried and concentrated. The residue obtained was purified by a column chromatography on a silica gel (dichloromethane: 10% aqueous ammonia-containing methanol=30:1) to obtain the title compound (59.1 g) as a pale yellow oil.

Workup

  1. temperaturewas refluxed for 15 hours
  2. concentrationthe reaction mixture was concentrated
  3. dissolutionthe resultant residue was dissolved in water
  4. extractionextracted with dichloromethane
  5. customdried
  6. concentrationconcentrated
  7. customThe residue obtained
  8. customwas purified by a column chromatography on a silica gel (dichloromethane: 10% aqueous ammonia-containing methanol=30:1)

Sources & evidence

ORD record
ord-294b873d65a84cbf92946f4a98cf0f7f
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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