Hydrochloric Acid → (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexylthio)ethyl]piperidine-3-carboxylic acid dihydrochloride

HRID 2186373Notes

Reaction equation

HRID 2186373 reaction equation
[OH:1][CH:2]([C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([O:34][CH3:35])[CH:32]=2)[N:27]=[CH:26][CH:25]=1)[CH2:3][CH2:4][C@@H:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][S:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:7][C@@H:6]1[C:20]([O:22]C)=[O:21].[OH-].[Na+].[ClH:38]>CO.C(OC(C)C)(C)C>[ClH:38].[ClH:38].[OH:1][CH:2]([C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([O:34][CH3:35])[CH:32]=2)[N:27]=[CH:26][CH:25]=1)[CH2:3][CH2:4][C@@H:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][S:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:7][C@@H:6]1[C:20]([OH:22])=[O:21]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131723279methyl (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexylthio)ethyl]piperidine-3-carboxylate

Product 1

HCID 70172304(3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexylthio)ethyl]piperidine-3-carboxylic acid dihydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 7914Diisopropyl EtherSolvent

Procedure

0.4 gof methyl (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexylthio)ethyl]piperidine-3-carboxylate was heated in 3 cm3 of methanol to which had been added 0.48 cm3 of 5N aqueous sodium hydroxide solution under an inert atmosphere for 16 hours. After concentrating the reaction mass under reduced pressure (5 kPa) at a temperature in the region of 40° C., the residue obtained was taken up in 5 cm3 of 6N hydrochloric acid and then 2.5 cm3 of methanol. The brown solution obtained was evaporated under the same conditions as above. The residue which resulted therefrom was taken up in 5 cm3 of diisopropylether, filtered off, and washed with 2 times 3 cm3 of the same solvent. The solid obtained was dried under reduced pressure (13 Pa) at a temperature in the region of 60° C. 0.37 g of (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexylthio)ethyl]piperidine-3-carboxylic acid dihydrochloride was obtained in the form of a solid with a brown color melting while softening in the region of 170° C.

Workup

  1. concentrationAfter concentrating the reaction mass under reduced pressure (5 kPa) at a temperature in the region of 40° C.
  2. customthe residue obtained
  3. customThe brown solution obtained
  4. customwas evaporated under the same conditions as above
  5. customThe residue which resulted
  6. filtrationfiltered off
  7. washwashed with 2 times 3 cm3 of the same solvent
  8. customThe solid obtained
  9. customwas dried under reduced pressure (13 Pa) at a temperature in the region of 60° C

Sources & evidence

ORD record
ord-726318e7a2714c9e94f84b049613e99b
Source dataset
uspto-grants-2002_06
Patent number
US06403610B1

Reaction notes

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