Hydrochloric Acid → HCID 70176831, compound

HRID 2186368Notes

Reaction equation

HRID 2186368 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][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH2:18][C@@H:17]1[CH2:31][C:32]([O:34]C)=[O:33].[OH-].[Na+].[ClH:38].O>O1CCOCC1>[ClH:38].[ClH:38].[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][CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]2)[CH2:18][C@@H:17]1[CH2:31][C:32]([OH:34])=[O:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86758159HCID 86758159, compound

Product 1

HCID 70176831HCID 70176831, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
60 °C

Procedure

A mixture of 0.3 g of methyl (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexylthio)ethyl]piperidine-3-acetate in 8 cm3 of dioxane in the presence of 0.5 cm3 of 5N aqueous sodium hydroxide solution was heated with stirring at a temperature in the region of 60° C. for 20 hours. After cooling to a temperature in the region of 20° C., the reaction mixture was evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. A foam with a yellow color was obtained, which product was purified by chromatography at atmospheric pressure on a column of silica gel (particle size 20-45 μm; diameter 1.6 cm; silica volume 40 cm3), elution was carried out with a chloroform/methanol/28% aqueous ammonia (12/3/0.5 by volume) mixture, and first a fraction of 125 cm3 and then approximately 10-cm3 fractions were collected. Fractions 3 to 7 were combined and then evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 0.27 g of a lacquer was obtained, which product was taken up in 5 cm3 of dioxane, 11 cm3 of 0.1N aqueous hydrochloric acid and 14 cm3 of distilled water. The dioxane was evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. and then the residual solution was lyophilized. 0.29 g of (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexylthio)-ethyl]piperidine-3-acetic acid dihydrochloride was obtained in the form of a lyophilizate with a white color.

Workup

  1. temperaturewas heated
  2. temperatureAfter cooling to a temperature in the region of 20° C.
  3. customthe reaction mixture was evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C
  4. customA foam with a yellow color was obtained
  5. customwhich product was purified by chromatography at atmospheric pressure on a column of silica gel (particle size 20-45 μm; diameter 1.6 cm; silica volume 40 cm3), elution
  6. customfirst a fraction of 125 cm3 and then approximately 10-cm3 fractions were collected
  7. customevaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C
  8. custom0.27 g of a lacquer was obtained
  9. customThe dioxane was evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C.

Sources & evidence

ORD record
ord-50640721d11b4503b7b03dae6f026991
Source dataset
uspto-grants-2002_06
Patent number
US06403610B1

Reaction notes

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