Potassium Carbonate → (4-Chlorophenyl){4-[(pyrrolidin-1-yl)methyl]phenyl}methanone

HRID 1820002Notes

Reaction equation

Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[O:10])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[NH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1>C(#N)C>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][N:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)=[CH:4][CH:5]=2)=[O:10])=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Acetonitrile (55 ml) was added to [4-(bromomethyl)phenyl](4-chlorophenyl)methanone (6.71 g, 21.7 mmol), potassium carbonate (5.99 g, 43.3 mmol) and pyrrolidine (3.62 ml, 43.3 mmol), and the mixture was stirred at 80° C. for 16 hrs. The solvent was concentrated, and diethyl ether was added to the residue. The mixture was extracted with 1N hydrochloric acid. The extract was basified with potassium carbonate, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and the solvent was evaporated under reduced pressure. The obtained residue was purified by alumina column chromatography (developing solvent; ethyl acetate) to give the title compound (4.79 g).

Workup

concentrationThe solvent was concentrated
additiondiethyl ether was added to the residue
extractionThe mixture was extracted with 1N hydrochloric acid
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saturated brine
customthe solvent was evaporated under reduced pressure
customThe obtained residue was purified by alumina column chromatography (developing solvent; ethyl acetate)

Sources & evidence

ORD record: ord-e1bfab7c44db4dd2b5ebd6a6cc3deb07
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601868B2

Reaction notes

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