Hydrochloric Acid → HCID 178517105, compound

HRID 1058622Notes

Reaction equation

HRID 1058622 reaction equation
Cl[C:2]1[C:11]2[N:12]=[C:13]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:14]([CH2:15][CH2:16][CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.Cl.[OH-].[Na+].C(=O)([O-])[O-:33].[K+].[K+]>O1CCOCC1>[OH:33][C:2]1[C:11]2[N:12]=[C:13]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:14]([CH2:15][CH2:16][CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 9930351HCID 9930351, compound

Product 1

HCID 178517105HCID 178517105, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 871 mg of 4-chloro-2-phenyl-1-[2-(4-piperidyl)ethyl]-1H-imidazo[4,5-c]quinoline and 2.5 ml of 6 N hydrochloric acid in 8 ml of 1,4-dioxane was refluxed for 3 hours. The reaction mixture was adjusted to pH 10 with 10% aqueous sodium hydroxide solution, and added with potassium carbonate, and then extracted with 1,2-dichloroethane. The extract was dried, and the solvent was evaporated. The resulting residue was washed with ethyl acetate to give 522 mg of pale brown crystals. Recrystallization from methanol gave pale brown crystals having the melting point of from 242.5 to 244° C.

Workup

  1. extractionextracted with 1,2-dichloroethane
  2. customThe extract was dried
  3. customthe solvent was evaporated
  4. washThe resulting residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-3d65692eaf3f41b9a8d70c93b1a94e30
Source dataset
uspto-grants-2003_02
Patent number
US06518265B1

Reaction notes

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