Hydrochloric Acid → HCID 70175216, compound

HRID 2186347Notes

Reaction equation

HRID 2186347 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][CH:9]=[C:8]2[CH2:15][CH2:16][CH2:17][C@@H:18]1[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][S:26][C:27]2[S:28][CH:29]=[CH:30][CH:31]=2)[CH2:20][C@@H:19]1[C:32]([O:34]C)=[O:33].[ClH:36]>CO.O.ClCCl.CO>[ClH:36].[ClH:36].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][CH:9]=[C:8]2[CH2:15][CH2:16][CH2:17][C@@H:18]1[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][S:26][C:27]2[S:28][CH:29]=[CH:30][CH:31]=2)[CH2:20][C@@H:19]1[C:32]([OH:34])=[O:33]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86758151HCID 86758151, compound

Product 1

HCID 70175216HCID 70175216, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
60 °C

Procedure

0.5 cm3 of 5N aqueous sodium hydroxide was added to a stirred solution of 0.34 g of methyl (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-ylthio)ethyl]piperidine-3-carboxylate in 3 cm3 of methanol and then the mixture was heated 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 5 cm3 of water and then acidified by addition of 1 cm3 of 35% hydrochloric acid. The mixture was again evaporated under reduced pressure under the same conditions as above; the residue obtained was taken up in 5 cm3 of a dichloromethane/methanol (90/10 by volume) mixture. The insoluble material was filtered off and then the solvent was evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 0.35 g of (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-ylthio)ethyl]piperidine-3-carboxylic acid dihydrochloride was obtained in the form of a solid with a beige color which melts with softening in the region of 150° C.

Workup

  1. customAfter evaporating the solvents under reduced pressure (5 kPa) at a temperature in the region of 40° C.
  2. customthe residue obtained
  3. customThe mixture was again evaporated under reduced pressure under the same conditions as above
  4. customthe residue obtained
  5. filtrationThe insoluble material was filtered off
  6. customthe solvent was evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-4cb9062afb35435aa589966af6b91900
Source dataset
uspto-grants-2002_06
Patent number
US06403610B1

Reaction notes

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