Hydrochloric Acid → (+)-2-phenyl-3-methyl-8-(1-(R)-[2-(R)-methylpiperidino]-2-hydroxyethyl)quinoline hydrochloride

HRID 1167185Notes

Reaction equation

HRID 1167185 reaction equation
[ClH:1].[C:2]1([C:8]2[C:17]([CH3:18])=[CH:16][C:15]3[C:10](=[C:11]([C@@H:19]([N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][C@H:23]4[CH3:28])[CH2:20][OH:21])[CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.O>[ClH:1].[C:2]1([C:8]2[C:17]([CH3:18])=[CH:16][C:15]3[C:10](=[C:11]([C@@H:19]([N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][C@H:23]4[CH3:28])[CH2:20][OH:21])[CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 9841835(+)-2-phenyl-3-methyl-8-(1-(R)-[2-(R)-methylpiperidino]-2-hydroxyethyl)quinoline

Product 1

HCID 21356542(+)-2-phenyl-3-methyl-8-(1-(R)-[2-(R)-methylpiperidino]-2-hydroxyethyl)quinoline hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

8.3 ml of a 0.1N hydrochloric acid solution are added to a solution of 0.3 g (0.832 mmol) of (+)-2-phenyl-3-methyl-8-(1-(R)-[2-(R)-methylpiperidino]-2-hydroxyethyl)quinoline in 3 ml of methanol. The solvents are evaporated and the salt obtained is dissolved in 10 ml of water. The solution is filtered, frozen with a bath of dry ice in acetone, and lyophilized overnight to provide 0.33 g of (+)-2-phenyl-3-methyl-8-(1-(R)-[2-(R)-methylpiperidino]-2-hydroxyethyl)quinoline hydrochloride in the form of a white solid; M.p.=68° C. (Yield: quantitative)

Workup

  1. customThe solvents are evaporated
  2. customthe salt obtained
  3. filtrationThe solution is filtered
  4. temperaturefrozen with a bath of dry ice in acetone

Sources & evidence

ORD record
ord-570e9d3012ab419da69d989ea1e60e59
Source dataset
uspto-grants-2003_09
Patent number
US06617336B1

Reaction notes

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