Diisopropylethylamine → 4-(8-Azabicyclo[3.2.1]oct-8-yl)-3-(trifluoromethyl)benzonitrile

HRID 586078Notes

Reaction equation

F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].Cl.[CH:15]12[NH:22][CH:19]([CH2:20][CH2:21]1)[CH2:18][CH2:17][CH2:16]2.C(N(CC)C(C)C)(C)C>CS(C)=O>[CH:19]12[N:22]([C:2]3[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=3[C:10]([F:13])([F:12])[F:11])[CH:15]([CH2:21][CH2:20]1)[CH2:16][CH2:17][CH2:18]2

Participants

Conditions

Temperature: 120 °C

Procedure

4-Fluoro-3-(trifluoromethyl)benzonitrile (1.35 g, 7.14 mmol), 8-aza-bicyclo[3.2.1]octane hydrochloride (1.26 g, 8.57 mmol), and N,N-diisopropylethylamine (1.79 g, 13.8 mmol) were combined in DMSO (15 mL) and heated at 120° C. for 24 hours. The mixture was allowed to cool to ambient temperature and partitioned between diethyl ether and saturated NaHCO3 solution. The separated aqueous phase was extracted with diethyl ether and the combined organic layers were washed with water, brine, dried (Na2SO4), filtered, and the filtrate was concentrated under reduced pressure to provide the title compound which was used in the next step without further purification.

Workup

temperatureto cool to ambient temperature
custompartitioned between diethyl ether and saturated NaHCO3 solution
extractionThe separated aqueous phase was extracted with diethyl ether
washthe combined organic layers were washed with water, brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-82e318687c99424895ebf2b28a41735b
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06933311B2

Reaction notes

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