4-Chloropyridine hydrochloride → HCID 20039822, compound

HRID 1762834Notes

Reaction equation

HRID 1762834 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.Cl[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1.C(=O)(O)[O-].[Na+]>C(O)CCC>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:11][CH2:12][N:13]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[CH2:14][CH2:15]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 818524-Chloropyridine hydrochlorideHCID 516892Sodium BicarbonateHCID 159258174-(4-Nitrophenyl)piperidine

Product 1

HCID 20039822HCID 20039822, compoundYield 4.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 4-(4-nitrophenyl)piperidine [J. Chem. Soc. (B), 128, 1970] (4.12 g), 4-chloropyridine hydrochloride (3.00 g), sodium bicarbonate (5.04 g) and n-butanol (60 ml) was heated under reflux for 48 hours and then evaporated. The residue was partitioned between water and ethyl acetate. The organic phase was washed with water, dried (Na2SO4) and evaporated to give a solid which was chromatographed on silica gel. The column was eluted initially with ethyl acetate and then the eluent polarity was gradually increased to ethyl acetate/methanol (10:1). Earlier fractions contained impurity and the product was eluted in the later fractions. The product-containing fractions were combined and evaporated, and the residue was crystallised from ethyl acetate to give the title compound, (0.25 g), m.p. 173°-174°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 hours
  3. customevaporated
  4. customThe residue was partitioned between water and ethyl acetate
  5. washThe organic phase was washed with water
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customto give a solid which
  9. customwas chromatographed on silica gel
  10. washThe column was eluted initially with ethyl acetate
  11. temperaturethe eluent polarity was gradually increased to ethyl acetate/methanol (10:1)
  12. washthe product was eluted in the later fractions
  13. customevaporated
  14. customthe residue was crystallised from ethyl acetate

Sources & evidence

ORD record
ord-c319fce322854a979592d9fa0a3565a8
Source dataset
uspto-grants-1989_05
Patent number
US04835165

Reaction notes

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