Hydrochloric Acid → HCID 9808246, compound

HRID 394701Notes

Reaction equation

HRID 394701 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH2:12][CH2:13][CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][S:23][C:24]3[S:25][CH:26]=[CH:27][CH:28]=3)[CH2:17][CH:16]1[CH2:29][C:30]([O:32]C)=[O:31])=[CH:9][C:8]([O:34][CH3:35])=[CH:7][CH:6]=2.[OH-].[Na+].[Cl:38]CCl.[ClH:41]>O.CCOCC.CC(C)=O.O1CCOCC1>[ClH:38].[ClH:41].[F:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH2:12][CH2:13][CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][S:23][C:24]3[S:25][CH:26]=[CH:27][CH:28]=3)[CH2:17][CH:16]1[CH2:29][C:30]([OH:32])=[O:31])=[CH:9][C:8]([O:34][CH3:35])=[CH:7][CH:6]=2

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 86586484HCID 86586484, compound

Product 1

HCID 9808246HCID 9808246, compound

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of 480 mg of methyl (3RS,4RS)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-3-acetate, 5 cm3 of dioxane and 2.25 cm3 of a 1 N aqueous sodium hydroxide solution was heated, with stirring, at a temperature in the region of 60° C. for 1 hour 30 minutes. After concentrating the reaction mixture under reduced pressure (5 kPa) at a temperature the region of 40° C., the residue obtained was taken up in 50 cm3 of water and 20 cm3 of ether. The aqueous phase was separated after settling out and then washed twice with 10 cm3 of ether. It was then acidified by pouring 2.25 cm3 of 1 N hydrochloric acid. The precipitate formed was dissolved by adding 75 cm3 of dichloromethane. The organic phase was separated after settling out, dried over magnesium sulfate, filtered, and then concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. The product obtained was then stirred in 30 cm3 of acetone. 4 cm3 of 4 N hydrochloric acid in dioxane were then poured over this solution. The reaction mixture was concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. and then 15 cm3 of acetone were added. This operation was repeated 5 times until a yellow solid was obtained, which solid was drained and then dried in a desiccator under reduced pressure (10 Pa) at a temperature of about 45° C. 395 mg of (3RS,4RS)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)-propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-3-acetic acid dihydrochloride were obtained in the form of a solid, which was off-white in color.

Workup

  1. concentrationAfter concentrating the reaction mixture under reduced pressure (5 kPa) at a temperature the region of 40° C.
  2. customthe residue obtained
  3. customThe aqueous phase was separated
  4. washwashed twice with 10 cm3 of ether
  5. additionby pouring 2.25 cm3 of 1 N hydrochloric acid
  6. customThe precipitate formed
  7. dissolutionwas dissolved
  8. customThe organic phase was separated
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C
  12. customThe product obtained
  13. concentrationThe reaction mixture was concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C.
  14. addition15 cm3 of acetone were added
  15. customwas obtained
  16. customdried in a desiccator under reduced pressure (10 Pa) at a temperature of about 45° C

Sources & evidence

ORD record
ord-2e065317d59b40f585cbdb1bbb6d6c23
Source dataset
uspto-grants-2003_08
Patent number
US06602884B2

Reaction notes

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