Hydrochloric Acid → HCID 70174653, compound

HRID 2186346Notes

Reaction equation

HRID 2186346 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][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[F:31])[CH2:18][C@@H:17]1[C:32]([O:34]C)=[O:33].[OH-].[Na+].[ClH:38]>CO.O>[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][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[F:31])[CH2:18][C@@H:17]1[C:32]([OH:34])=[O:33]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86758150HCID 86758150, compound

Product 1

HCID 70174653HCID 70174653, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.12 g of methyl (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(2-fluorophenylthio)ethyl]piperidine-3-carboxylate and 0.6 cm3 of N aqueous sodium hydroxide in 1.8 cm3 of methanol was stirred for 20 hours at a temperature in the region of 60° C. The reaction mixture was evaporated 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 acidified with 1 cm3 of 2N aqueous hydrochloric acid. The mixture was again evaporated under the same conditions as above and then the new residue was triturated in 5 cm3 of a dichloromethane/methanol (90/10 by volume) mixture. After filtering and evaporating the filtrate under reduced pressure (5 kPa) at a temperature in the region of 40° C., the residue obtained was triturated in 3 cm3 of diisopropyl ether. The insoluble material was filtered off, washed with 2 times 1 cm3 of diisopropyl ether, and dried in the air. 0.14 g of (3R,4R)-4-(3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(2-fluorophenylthio)ethyl]piperidine-3-carboxylic acid hydrochloride was obtained in the form of a solid with a beige color which melts with softening at approximately 148° C.

Workup

  1. customThe reaction mixture was evaporated 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 the same conditions as above and then the new residue
  4. customwas triturated in 5 cm3 of a dichloromethane/methanol (90/10 by volume) mixture
  5. filtrationAfter filtering
  6. customevaporating the filtrate under reduced pressure (5 kPa) at a temperature in the region of 40° C.
  7. customthe residue obtained
  8. customwas triturated in 3 cm3 of diisopropyl ether
  9. filtrationThe insoluble material was filtered off
  10. washwashed with 2 times 1 cm3 of diisopropyl ether
  11. customdried in the air

Sources & evidence

ORD record
ord-8a49d2742b4e4304ac6c11d5b1c5aa99
Source dataset
uspto-grants-2002_06
Patent number
US06403610B1

Reaction notes

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