4-Chloropyridine hydrochloride → HCID 18620726, compound

HRID 1861705Notes

Reaction equation

HRID 1861705 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][C:12]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[NH:19][CH2:18][CH2:17]3)=[O:13])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].Cl.Cl[C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1>C(O)CCC>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][C:12]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[N:19]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[CH2:18][CH2:17]3)=[O:13])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 818524-Chloropyridine hydrochlorideHCID 10334985HCID 10334985, compound

Product 1

HCID 18620726HCID 18620726, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixed solution of 3-(1-acetyl-4-piperidinyl)-1-(2,3-dihydroindol-5-yl)-1-propanone (0.4 g, 1.33 mmol) and 4-chloropyridine hydrochloride (0.2 g, 1.33 mmol) in 1-butanol (4 ml) was heated and stirred for 3 hours. The solvent was then distilled off and the residue was dissolved in 5% sodium hydroxide/H2O-ethyl acetate and extracted with ethyl acetate. The extract was washed with saturated NaCl/H2O and dried over MgSO4. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel column chromatography (eluent: ethyl acetate-methanol=10:1) to provide the title compound (0.35 g) as colorless powders melting at 157-158° C.

Workup

  1. distillationThe solvent was then distilled off
  2. dissolutionthe residue was dissolved in 5% sodium hydroxide/H2O-ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated NaCl/H2O
  5. dry with materialdried over MgSO4
  6. distillationThe solvent was then distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate-methanol=10:1)

Sources & evidence

ORD record
ord-12d3ea6a6f4f4714b9240fa3e4c0fb4b
Source dataset
uspto-grants-2003_03
Patent number
US06534496B1

Reaction notes

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