Hydrochloric Acid → HCID 70172587, compound

HRID 2186354Notes

Reaction equation

HRID 2186354 reaction equation
[OH:1][CH:2]([C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([O:33][CH3:34])[CH:31]=2)[N:26]=[CH:25][CH:24]=1)[CH2:3][CH2:4][C@@H:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][S:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)[CH2:7][C@@H:6]1[C:19]([O:21]C)=[O:20].[OH-].[Na+].[ClH:37]>CO>[ClH:37].[ClH:37].[OH:1][CH:2]([C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([O:33][CH3:34])[CH:31]=2)[N:26]=[CH:25][CH:24]=1)[CH2:3][CH2:4][C@@H:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][S:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)[CH2:7][C@@H:6]1[C:19]([OH:21])=[O:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53238634HCID 53238634, compound

Product 1

HCID 70172587HCID 70172587, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.45 g of methyl (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(2-thienylthio)ethyl]piperidine-3-carboxylate, 3.5 cm3 of methanol, and 0.54 cm3 of 5N aqueous sodium hydroxide was heated with stirring at a temperature in the region of 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 3 cm3 of a 6N aqueous hydrochloric acid solution. 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 2 times 1 cm3 of this mixture. The filtrate was dried over sodium sulfate and then concentrated under reduced pressure (5 kPa) at a temperature in the region of 4° C. After drying in the air, 0.16 g of (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(2-thienylthio)ethyl]piperidine-3-carboxylic acid dihydrochloride was obtained in the form of a beige solid which melts, with softening, at approximately 148° C.

Workup

  1. temperaturewas heated
  2. customAfter evaporating the solvents under reduced pressure (5 kPa) at a temperature in the region of 40° C.
  3. customthe residue obtained
  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 2 times 1 cm3 of this mixture
  9. dry with materialThe filtrate was dried over sodium sulfate
  10. concentrationconcentrated under reduced pressure (5 kPa) at a temperature in the region of 4° C
  11. customAfter drying in the air

Sources & evidence

ORD record
ord-c7fa566cc92b4a26bafe184597da8749
Source dataset
uspto-grants-2002_06
Patent number
US06403610B1

Reaction notes

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