Potassium Carbonate → 1-[4-(4-Benzyl-piperazin-1-yl)-2-hydroxy-5-methoxy-phenyl]ethanone

HRID 2266163Notes

Reaction equation

C([O:8][C:9]1[CH:14]=[C:13](F)[C:12]([O:16][CH3:17])=[CH:11][C:10]=1[C:18](=[O:20])[CH3:19])C1C=CC=CC=1.[CH2:21]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:21]([N:28]1[CH2:33][CH2:32][N:31]([C:13]2[C:12]([O:16][CH3:17])=[CH:11][C:10]([C:18](=[O:20])[CH3:19])=[C:9]([OH:8])[CH:14]=2)[CH2:30][CH2:29]1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 135 °C

Procedure

To a solution of 1-(2-Benzyloxy-4-fluoro-5-methoxy-phenyl)-ethanone (4.25 g, 15.5 mmol) in 3 mL DMF was added 1-benzyl-piperazine (5.4 mo, 30.9 mmol) and potassium carbonate (4.28 g, 30.9 mmol). The reaction mixdture was heated under nitrogen to 130-140° C. for 18 hours. The reaction mixture was cooled to room temperature, poured into ice water, and extracted with EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated under reduced pressure. The resulting residue was purified by flash chromatography on silica gel (hexanes: ethyl acetate 8.5:1.5) to yield 4.5 g (73% ) of 1-[4-(4-Benzyl-piperazin-1-yl)-2-hydroxy-5-methoxy-phenyl]-ethanone as a solid. MP=90-92° C.

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionextracted with EtOAc
washThe combined organic layers were washed with brine
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated under reduced pressure
customThe resulting residue was purified by flash chromatography on silica gel (hexanes: ethyl acetate 8.5:1.5)

Sources & evidence

ORD record: ord-46bd162f1760482d898c32883e83905b
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858632B2

Reaction notes

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