Hydrogen chloride-ethyl acetate → 4-bromo-N-[(3R,4R)-3-(3,4-dichlorophenyl)piperidin-4-yl]-N-methylbenzamide
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]([CH3:32])[C@@H:11]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][C@H:12]2[C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=2)=[O:9])=[CH:4][CH:3]=1.Cl.C(OCC)(=O)C>C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:10]([C@@H:11]2[CH2:16][CH2:15][NH:14][CH2:13][C@H:12]2[C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=2)[CH3:32])=[O:9])=[CH:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of the compound (1.09 g) obtained in step 2 in ethyl acetate (8 mL) was added 4N hydrogen chloride/ethyl acetate (8 mL), and the mixture was stirred at 50° C. for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in a mixture of ethyl acetate and acetonitrile. This solution was washed with 1N aqueous sodium hydroxide solution and dried, and the solvent was evaporated under reduced pressure to give 4-bromo-N-[(3R,4R)-3-(3,4-dichlorophenyl)piperidin-4-yl]-N-methylbenzamide (0.830 g, 93%) as a white powder.
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- dissolutionthe residue was dissolved in a mixture of ethyl acetate and acetonitrile
- washThis solution was washed with 1N aqueous sodium hydroxide solution
- customdried
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-512c961a56e64d92a63ed61a9a98188a
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08470816B2
Reaction notes
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