Hydrochloric Acid → HCID 70174049, compound
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][N:26]=2)[CH2:18][C@@H:17]1[C:31]([O:33]C)=[O:32].[ClH:35]>>[ClH:35].[ClH:35].[ClH:35].[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][N:26]=2)[CH2:18][C@@H:17]1[C:31]([OH:33])=[O:32]Participants
Conditions
- Temperature
- 100 °C
Procedure
A solution of 0.5 g of methyl (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(pyridin-2-ylthio)ethyl]piperidine-3-carboxylate in 7.8 cm3 of 6N hydrochloric acid was heated with stirring at a temperature in the region of 100° C. for 2 hours. After concentrating the reaction mixture to dryness under reduced pressure (5 kPa) at a temperature in the region of 80° C. the residue obtained was triturated in 10 cm3 of diisopropyl ether. The insoluble material was filtered off and then dried under reduced pressure (13 kPa) at a temperature in the region of 60° C. 0.55 g of (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(pyridin-2-ylthio)ethyl]piperidine-3-carboxylic acid trihydrochloride was obtained in the form of a solid with a cream color which melts with softening in the region of 165° C.
Workup
- concentrationAfter concentrating the reaction mixture to dryness under reduced pressure (5 kPa) at a temperature in the region of 80° C. the residue
- customobtained
- customwas triturated in 10 cm3 of diisopropyl ether
- filtrationThe insoluble material was filtered off
- customdried under reduced pressure (13 kPa) at a temperature in the region of 60° C
Sources & evidence
- ORD record
- ord-fa63fed9457c427f8c6fc17f1d6c80d9
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06403610B1
Reaction notes
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