Dimethylformamide → 1-[7-(2-Methoxyethoxy)-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran-5-yl]-4-(4-methylphenyl)piperazine

HRID 1850500Notes

Reaction equation

CN(C=O)C.[CH3:6][C:7]1([CH3:32])[CH2:11][C:10]2[C:12]([CH3:31])=[C:13]([N:18]3[CH2:23][CH2:22][N:21]([C:24]4[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=4)[CH2:20][CH2:19]3)[C:14]([CH3:17])=[C:15]([OH:16])[C:9]=2[O:8]1.Br[CH2:34][CH2:35][O:36][CH3:37].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O>[CH3:37][O:36][CH2:35][CH2:34][O:16][C:15]1[C:9]2[O:8][C:7]([CH3:32])([CH3:6])[CH2:11][C:10]=2[C:12]([CH3:31])=[C:13]([N:18]2[CH2:19][CH2:20][N:21]([C:24]3[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=3)[CH2:22][CH2:23]2)[C:14]=1[CH3:17]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of DMF (5 mL) containing 2,2,4,6-tetramethyl-5-[4-(4-methylphenyl)piperazin-1-yl]-2,3-dihydro-1-benzofuran-7-ol (200 mg, 0.546 mmol) synthesized in Example 72, 1-bromo-2-methoxyethane (382 mg, 2.75 mmol) and potassium carbonate (380 mg, 2.75 mmol) were added, and the mixture was stirred at 100° C. for 24 hours. After cooled to room temperature, water was added to the mixture, and extraction was performed using ethyl acetate. The extract was dried using anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 100:0-90:10) to obtain 33.5 mg of the title compound (yield 14%). Melting point was 118 to 120° C. (hexane).

Workup

additionwere added
temperatureAfter cooled to room temperature
customThe extract was dried
customthe solvent was removed under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 100:0-90:10)

Sources & evidence

ORD record: ord-2263fa93ab3047f9860824474911f887
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957069B2

Reaction notes

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