Hydrochloric Acid → HCID 70174216, compound

HRID 2186340Notes

Reaction equation

HRID 2186340 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[CH2:13][CH2:14][CH2:15][C@@H:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][S:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=2)[CH2:18][C@@H:17]1[C:32]([O:34]C)=[O:33].[ClH:36]>CO.[OH-].[Na+].O>[ClH:36].[ClH:36].[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[CH2:13][CH2:14][CH2:15][C@@H:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][S:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=2)[CH2:18][C@@H:17]1[C:32]([OH:34])=[O:33]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 86758142HCID 86758142, compound

Product 1

HCID 70174216HCID 70174216, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.54 g of methyl (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(3-fluorophenylthio)ethyl]piperidine-3-carboxylate in 4 cm3 of methanol and 0.8 cm3 of 5N aqueous sodium hydroxide was heated with stirring at 60° C. for 20 hours. After evaporating the solvents under reduced pressure (5 kPa) at a temperature in the region of 40° C. the residue obtained was taken up in 10 cm3 of water and then acidified with 0.4 cm3 of concentrated hydrochloric acid. The solution was evaporated under the same conditions and then the residue obtained was triturated in a dichloromethane/methanol (90/10 by volume) mixture. The insoluble material was filtered off and washed with 5 cm3 of dichloromethane. The filtrate was dried over sodium sulfate and then concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. The residue was triturated in 10 cm3 of diisopropyl ether and then 1 cm3 of a 5N solution of hydrochloric acid in diisopropyl ether was added with stirring. The crystals were separated by filtration and then washed with 2 times 5 cm3 of diisopropyl ether. After drying in the air, 0.45 g of (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(3-fluorophenylthio) ethyl]piperidine-3-carboxylic acid dihydrochloride was obtained in the form of an amorphous solid with a pale yellow color which melts in the region of 140° C. with softening.

Workup

  1. temperaturewas heated
  2. customAfter evaporating the solvents under reduced pressure (5 kPa) at a temperature in the region of 40° C. the residue
  3. customobtained
  4. customThe solution was evaporated under the same conditions
  5. customthe residue obtained
  6. customwas triturated in a dichloromethane/methanol (90/10 by volume) mixture
  7. filtrationThe insoluble material was filtered off
  8. washwashed with 5 cm3 of dichloromethane
  9. dry with materialThe filtrate was dried over sodium sulfate
  10. concentrationconcentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C
  11. customThe residue was triturated in 10 cm3 of diisopropyl ether
  12. addition1 cm3 of a 5N solution of hydrochloric acid in diisopropyl ether was added
  13. stirringwith stirring
  14. customThe crystals were separated by filtration
  15. washwashed with 2 times 5 cm3 of diisopropyl ether
  16. customAfter drying in the air

Sources & evidence

ORD record
ord-24266de2479946cc8ac12162fec3be2d
Source dataset
uspto-grants-2002_06
Patent number
US06403610B1

Reaction notes

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