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

HRID 38419Notes

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 mixture 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-58d500c56e93410a873b6bedfc76fc9f
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524725B2

Reaction notes

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