Hydrochloric Acid → 4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-carboxylic acid dihydrochloride

HRID 394976Notes

Reaction equation

HRID 394976 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH2:12][CH2:13][CH2:14][C:15]1([C:29]([O:31]CC)=[O:30])[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][S:23][CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:17][CH2:16]1)=[CH:9][C:8]([O:34][CH3:35])=[CH:7][CH:6]=2.[ClH:36]>ClCCl.CO>[ClH:1].[ClH:36].[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH2:12][CH2:13][CH2:14][C:15]1([C:29]([OH:31])=[O:30])[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][S:23][CH:24]3[CH2:25][CH2:26][CH2:27][CH2:28]3)[CH2:17][CH2:16]1)=[CH:9][C:8]([O:34][CH3:35])=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22468662Ethyl 4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(2-(cyclopentylthio)ethyl]piperidine-4-carboxylate

Product 1

HCID 696831844-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-carboxylic acid dihydrochloride

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 0.55 g of ethyl 4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]-piperidine-4-carboxylate in 8 cm3 of aqueous 6 N hydrochloric acid was heated at a temperature in the region of 100° C., with stirring and under an inert atmosphere, for 5 hours. After stirring for 18 hours at a temperature in the region of 20° C., the solution obtained was concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. The evaporation residue obtained was taken up in 10 cm3 of a mixture of dichloromethane/methanol (90/10 by volume) and then concentrated under the same conditions as above. 0.59 g of 4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-carboxylic acid dihydrochloride was obtained in the form of a foam melting at 129° C. with softening.

Workup

  1. stirringAfter stirring for 18 hours at a temperature in the region of 20° C.
  2. customthe solution obtained
  3. concentrationwas concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C
  4. customThe evaporation residue obtained
  5. concentrationconcentrated under the same conditions as above

Sources & evidence

ORD record
ord-e34eaf532a6b4017b03bf4390e513278
Source dataset
uspto-grants-2003_08
Patent number
US06603005B2

Reaction notes

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