Methanol → HCID 22468680, compound

HRID 394985Notes

Reaction equation

HRID 394985 reaction equation
[OH-].[Na+].CO.[Cl:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[CH2:16][CH2:17][CH2:18][C:19]1([C:33]([O:35]CC)=[O:34])[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][S:27][C:28]3[S:29][CH:30]=[CH:31][CH:32]=3)[CH2:21][CH2:20]1)=[CH:13][C:12]([O:38][CH3:39])=[C:11]([O:40][CH3:41])[CH:10]=2>O1CCOCC1>[Cl:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[CH2:16][CH2:17][CH2:18][C:19]1([C:33]([OH:35])=[O:34])[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][S:27][C:28]3[S:29][CH:30]=[CH:31][CH:32]=3)[CH2:21][CH2:20]1)=[CH:13][C:12]([O:38][CH3:39])=[C:11]([O:40][CH3:41])[CH:10]=2

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 22470697HCID 22470697, compound

Product 1

HCID 22468680HCID 22468680, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

26 cm3 of aqueous 5N sodium hydroxide and 20 cm3 of methanol were added to a solution of 1.47 g of ethyl 4-[3-(3-chloro-6,7-dimethoxyquinolin-4-yl)propyl]-1-[2-(thiophen-2-ylthio)ethyl]piperidine-4-carboxylate in 20 cm3 of dioxane, with stirring and at a temperature in the region of 20° C., and the mixture was then maintained at a temperature of about 70° C. for 21 hours. The reaction mixture was concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue obtained was purified by chromatography under a pressure of 50 kPa of argon, on a column of silica gel (particle size 40-63μ; mass 60 g), eluting with a mixture of dichloromethane/methanol/aqueous ammonia (12/3/0.5 by volume). Fractions 11 to 25 were combined and then concentrated to dryness under the above conditions. 1.03 g of 4-[3-(3-chloro-6,7-dimethoxy-quinolin-4-yl)propyl]-1-[2-(thiophen-2-ylthio)ethyl]-piperidine-4-carboxylic acid was obtained in the form of a white solid melting at 214° C.

Workup

  1. temperaturethe mixture was then maintained at a temperature of about 70° C. for 21 hours
  2. concentrationThe reaction mixture was concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  3. customThe residue obtained
  4. customwas purified by chromatography under a pressure of 50 kPa of argon, on a column of silica gel (particle size 40-63μ; mass 60 g)
  5. washeluting with a mixture of dichloromethane/methanol/aqueous ammonia (12/3/0.5 by volume)
  6. concentrationconcentrated to dryness under the above conditions

Sources & evidence

ORD record
ord-068f5feaa04142329d242c571a1d6c60
Source dataset
uspto-grants-2003_08
Patent number
US06603005B2

Reaction notes

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