4-Chloropyridine hydrochloride → 4-[1-(4-Pyridyl)piperidin-4-yl]benzenesulphonamide

HRID 1762840Notes

Reaction equation

HRID 1762840 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([NH2:16])(=[O:15])=[O:14])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.Cl.Cl[C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1.C(=O)(O)[O-].[Na+]>C(O)CC(C)C>[N:22]1[CH:23]=[CH:24][C:19]([N:1]2[CH2:6][CH2:5][CH:4]([C:7]3[CH:12]=[CH:11][C:10]([S:13]([NH2:16])(=[O:14])=[O:15])=[CH:9][CH:8]=3)[CH2:3][CH2:2]2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 818524-Chloropyridine hydrochlorideHCID 516892Sodium BicarbonateHCID 183484304-Piperidin-4-YL-benzenesulfonamide

Product 1

HCID 200398364-[1-(4-Pyridyl)piperidin-4-yl]benzenesulphonamide

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Procedure

A mixture of the product of part (iii) above (3.75 g), 4-chloropyridine hydrochloride (2.34 g), sodium bicarbonate (3.93 g) and isoamyl alcohol (60 ml) was heated under reflux for 30 hours and then evaporated. The residue was triturated with water and the mixture was filtered. The solid was washed well with water and crystallised from methanol/water to give the title compound (0.43 g), m.p. 295° (with decomp).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 hours
  3. customevaporated
  4. customThe residue was triturated with water
  5. filtrationthe mixture was filtered
  6. washThe solid was washed well with water
  7. customcrystallised from methanol/water

Sources & evidence

ORD record
ord-974fcb6d8bc84ab8b2bb8ac014e34672
Source dataset
uspto-grants-1989_05
Patent number
US04835165

Reaction notes

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