Hydrochloric Acid → HCID 23157158, compound
Reaction equation
C([N:8]1CC=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2C)[CH2:10][CH2:9]1)C1C=CC=CC=1.[ClH:21].Cl.[O:23]1[CH2:28][CH2:27]OCC1>>[Cl:21][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH:11]1[CH2:10][CH2:9][NH:8][CH2:27][CH:28]1[OH:23]Participants
Procedure
Tert-butyl (3RS,4RS)-4-(2-chlorophenyl)-3-hydroxypiperidine-1-carboxylate was obtained as a colorless amorphous substance in the same manner as in Production Example 12-2, for which, however, the compound obtained in the above 2 was used in place of 1-benzyl-4-o-tolyl-1,2,3,6-tetrahydropyridine used in Production Example 12-2 and the step of converting the product into its hydrochloride was omitted. In a nitrogen atmosphere, 4 N hydrogen chloride-dioxane solution was added to the above compound, and stirred at room temperature for 1.5 hours. The solvent was evaporated off under reduced pressure, aqueous saturated sodium hydrogencarbonate solution was added to the residue, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure to obtain (3RS,4RS)-4-(2-chlorophenyl)piperidin-3-ol as a white solid.
Workup
- customhowever, the compound obtained in the above 2
- customThe solvent was evaporated off under reduced pressure, aqueous saturated sodium hydrogencarbonate solution
- additionwas added to the residue
- extractionextracted with ethyl acetate
- washThe ethyl acetate layer was washed with saturated saline water
- dry with materialdried with anhydrous sodium sulfate
- customThe solvent was evaporated off under reduced pressure
Sources & evidence
- ORD record
- ord-a5ba79dc2c7f4052886a74d1afbfcdb6
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07855294B2
Reaction notes
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