Water → HCID 24780777, compound

HRID 2403544Notes

Reaction equation

CON(C)[C:4](=[O:30])[CH:5]=[C:6]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[CH2:16][CH2:15]2)[CH2:8][CH2:7]1.[CH3:32][Mg]Cl.O>O1CCCC1>[F:29][C:26]([F:28])([F:27])[C:22]1[CH:21]=[C:20]([N:17]2[CH2:16][CH2:15][N:14]([CH2:13][CH2:12][CH:9]3[CH2:10][CH2:11][C:6](=[CH:5][C:4](=[O:30])[CH3:32])[CH2:7][CH2:8]3)[CH2:19][CH2:18]2)[CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 5 °C

Procedure

To a solution of 114 mg (0.25 mmol) of N-methoxy-N-methyl-2-(4-{2-[4-(3-trifluoromethylphenyl)piperazin-1-yl]ethyl}-cyclohexylidene)acetamide in 5 mL of dry tetrahydrofuran cooled to 0° C. is added 0.2 mL (0.50 mmol) of a 22% methylmagnesium chloride solution in tetrahydrofuran. The mixture is warmed up to 5° C. and stirred for 90 minutes. Hydrolysis is performed by slow addition of 3 mL of water. The product is extracted 3 times with ethyl acetate. The organic phases are combined, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The obtained residue is purified over 5 g of silica gel (eluant dichloromethane/methanol 95/5) to give 43 mg (44%) of 1-(4-{2-[4-(3-trifluoromethylphenyl)piperazin-1-yl]ethyl}cyclohexylidene)propan-2-one as an oil.

Workup

customHydrolysis
extractionThe product is extracted 3 times with ethyl acetate
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe obtained residue is purified over 5 g of silica gel (eluant dichloromethane/methanol 95/5)

Sources & evidence

ORD record: ord-abd8b7d9e8e544df96ac3cc43db39e11
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802678B2

Reaction notes

Loading…