Hydrochloric Acid → HCID 69900139, compound

HRID 2414966Notes

Reaction equation

HRID 2414966 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.Cl>O.CCOCC.CC(C)=O.O1CCOCC1>[ClH:38].[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 69900139HCID 69900139, compound

Reagents, catalysts & solvents 4

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

Conditions

Temperature
60 °C

Procedure

A solution of 195 mg of methyl (3SR,4RS)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-thienylthio)ethyl]piperidine-3-acetate, 2 cm3 of dioxane and 0.9 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. After concentrating the reaction mixture under reduced pressure (5 kPa) at a temperature in the region of 40° C., the residue obtained was taken up in 20 cm3 of water and 10 cm3 of ether. The aqueous phase was separated after settling out and then acidified by adding 0.9 cm3 of 1 N hydrochloric acid. The precipitate formed was dissolved with 20 cm3 of dichloromethane. The organic phase was washed twice with 10 cm3 of a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. The product obtained was then stirred in 20 cm3 of acetone. A solution of 2 cm3 of 4 N hydrochloric acid in dioxane was 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 5 cm3 of acetone were added. This operation was repeated 4 times. 155 mg of (3SR,4RS)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-thienylthio)ethyl]piperidine-3-acetic acid hydrochloride 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 in the region of 40° C.
  2. customthe residue obtained
  3. customThe aqueous phase was separated
  4. additionby adding 0.9 cm3 of 1 N hydrochloric acid
  5. customThe precipitate formed
  6. washThe organic phase was washed twice with 10 cm3 of a saturated aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C
  10. customThe product obtained
  11. concentrationThe reaction mixture was concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C.
  12. addition5 cm3 of acetone were added

Sources & evidence

ORD record
ord-a0013ec4faf3416cac941447c4ba2592
Source dataset
uspto-grants-2004_11
Patent number
US06815547B2

Reaction notes

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