Benzene, 1-bromo-4-(trifluoromethyl)- → Tert-butyl 1-[4-(trifluoromethyl)phenyl]piperidin-4-ylcarbamate
Reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6](Br)=[CH:5][CH:4]=1.C(P(C(C)C)C(C)C)(C)C.[NH:22]1[CH2:27][CH2:26][CH:25]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:24][CH2:23]1>CC([O-])=O.CC([O-])=O.[Pd+2]>[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6]([N:22]2[CH2:23][CH2:24][CH:25]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:33])([CH3:32])[CH3:34])[CH2:26][CH2:27]2)=[CH:5][CH:4]=1Participants
5
Conditions
- Temperature
- 110 °C
Procedure
A 100 mL round bottom flask was mixed with 4-triflouromethylbromobenzene (3.2 g, 15.0 mmol), triisopropylphosphine (10.0 mg, 0.062 mmol), Pd(OAc)2 (3.0 mg, 0.013 mmol) and xylenes (50 mL). The reaction mixture was allowed to heat at 110° C. for a period of 30 min at which it was mixed with tert-butyl piperidin-4-ylcarbamate (1.0 g 5.0 mmol). The reaction mixture stirred at 120° C. for 4.0 hours and then cooled to RT. The reaction mixture was partitioned between EtOAc and saturated NaHCO3. The organics were dried over MgSO4 and concentrated to a crude oil. The oil was purified using silica gel chromatography (90% hexanes/10% EtOAc) to yield a total of 472 mg of mostly pure solid.
Workup
- temperaturecooled to RT
- customThe reaction mixture was partitioned between EtOAc and saturated NaHCO3
- dry with materialThe organics were dried over MgSO4
- concentrationconcentrated to a crude oil
- customThe oil was purified
- customto yield a total of 472 mg of mostly pure solid
Sources & evidence
- ORD record
- ord-68a810d8380040819f1ac9de657a7a8c
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07183290B2
Reaction notes
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