Hydrochloric Acid → HCID 70174515, compound
Reaction equation
C([N:9]1[CH2:14][CH2:13][C@@H:12]([CH2:15][CH2:16][CH2:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([O:28][CH3:29])[CH:26]=3)[N:21]=[CH:20][CH:19]=2)[C@@H:11]([C:30]([OH:32])=[O:31])[CH2:10]1)(=O)C1C=CC=CC=1.[ClH:33]>>[ClH:33].[CH3:29][O:28][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[C:18]2[CH2:17][CH2:16][CH2:15][C@@H:12]1[CH2:13][CH2:14][NH:9][CH2:10][C@@H:11]1[C:30]([OH:32])=[O:31]Participants
Procedure
8.8 g of (3R,4R)-1-benzoyl-4-[3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylic acid were heated, with stirring, in 200 cm3 of 5N aqueous hydrochloric acid at a temperature in the region of 100° C. for 48 hours. The reaction mixture was concentrated under reduced pressure (5 kPa) at a temperature in the region of 50° C. The residue was taken up in 100 cm3 of acetone. The mixture was concentrated under reduced pressure (5 kPa) at a temperature in the region of 60° C. This operation was repeated an additional two times. The residue was finally triturated in 100 cm3 of acetone until it crystallized. After filtering off the crystals and drying in a desiccator under reduced pressure (10 kPa), 7.2 g of (3R,4R)-4-[3-(6-methoxyquinolin4-yl)propyl]piperidine-3-carboxylic acid hydrochloride were obtained in the form of a beige solid melting at approximately 270° C. (melting with softening).
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure (5 kPa) at a temperature in the region of 50° C
- concentrationThe mixture was concentrated under reduced pressure (5 kPa) at a temperature in the region of 60° C
- customThe residue was finally triturated in 100 cm3 of acetone until it
- customcrystallized
- filtrationAfter filtering off the crystals
- customdrying in a desiccator under reduced pressure (10 kPa)
Sources & evidence
- ORD record
- ord-e2aeb6f299ac49fe8d5e926e2e89b8b6
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06403610B1
Reaction notes
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