Diisopropylethylamine → 4-(8-Azabicyclo[3.2.1]oct-8-yl)-2-chlorobenzonitrile

HRID 586075Notes

Reaction equation

HRID 586075 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Cl.[CH:12]12[NH:19][CH:16]([CH2:17][CH2:18]1)[CH2:15][CH2:14][CH2:13]2.C(N(CC)C(C)C)(C)C>CS(C)=O>[CH:16]12[N:19]([C:8]3[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([Cl:1])[CH:9]=3)[CH:12]([CH2:18][CH2:17]1)[CH2:13][CH2:14][CH2:15]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1090002-Chloro-4-fluorobenzonitrileHCID 5222728-Azabicyclo[3.2.1]octane hydrochloride

Product 1

HCID 223376884-(8-Azabicyclo[3.2.1]oct-8-yl)-2-chlorobenzonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

2-Chloro-4-fluorobenzonitrile (0.97 g, 6.2 mmol), 8-aza-bicyclo[3.2.1]octane hydrochloride (0.92 g, 6.2 mmol), and N,N-diisopropylethylamine (1.6 g, 12 mmol) were combined in DMSO (15 mL) and heated at 120° C. for 16 hours. The mixture was allowed to cool to ambient temperature and partitioned between diethyl ether and saturated NaHCO3 solution. The aqueous phase was separated and extracted with diethyl ether. The organic layers were combined, 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

  1. temperatureto cool to ambient temperature
  2. custompartitioned between diethyl ether and saturated NaHCO3 solution
  3. customThe aqueous phase was separated
  4. extractionextracted with diethyl ether
  5. washwashed with water, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2980d8bb4f7a466abaf745c50dcf08fd
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Reaction notes

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