Potassium Hydroxide → 4-(4-Bromophenyl)-4-methylpiperidine
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:19])[CH2:13][CH2:12][N:11](C(OCC)=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-].[K+]>CCO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:19])[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of ethyl 4-(4-bromophenyl)-4-methylpiperidine-1-carboxylate (284) (5.36 g, 16 mmol) in EtOH (75 mL) was added KOH (17.9 g, 320 mmol). The resulting mixture was stirred at 80° C. for overnight before being cooled down to RT. The solvent was removed and the residue was partitioned in water (30 mL) and DCM (20 mL). The layers were separated and the aqueous layer was extracted with DCM (10 mL×5). The combined organic layers were washed with brine, dried, and concentrated in vacuo to give crude 4-(4-bromophenyl)-4-methylpiperidine (285) in quantitative yield, which was used directly in next step without further purification.
Workup
- temperaturebefore being cooled down to RT
- customThe solvent was removed
- customthe residue was partitioned in water (30 mL)
- customThe layers were separated
- extractionthe aqueous layer was extracted with DCM (10 mL×5)
- washThe combined organic layers were washed with brine
- customdried
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-8f7f1d4951ec4910aadeae15e8fbccbd
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09382246B2
Reaction notes
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