Tetrahydrofuran → HCID 66924408, compound
Reaction equation
Cl.[F:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12]N2CCCCC2)[C:4]=1[C:5]#[N:6].C([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])C.[Cl:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1.O1CCC[CH2:37]1>>[Cl:26][C:27]1[CH:35]=[CH:34][C:30]([C:31]([N:21]2[CH2:22][CH2:23][CH:37]([CH2:12][O:11][C:7]3[CH:8]=[CH:9][CH:10]=[C:3]([F:2])[C:4]=3[C:5]#[N:6])[CH2:25][CH2:24]2)=[O:32])=[CH:29][CH:28]=1Participants
Procedure
2-Fluoro-6-(piperidin-1-ylmethoxy)benzonitrile hydrochloride (122 mg; 0.45 mmol) was suspended in 2 mL of tetrahydrofuran, and in one portion triethylamine was added (0.2 mL. 1.4 mmol) to the mixture at room temperature. 4-Chlorobenzoyl chloride (0.06 mL; 0.45 mmol) was then added, and stirred at room temperature for 16 hrs. Reaction was quenched with 2 mL 1 N HCl. Mixture was extracted twice with 10 mL of ethyl acetate and organic layers combined. Mixture was then washed with sat. NaHCO3, brine and dried over MgSO4. Mixture was filtered and concentrated to an oil. Material was purified via flash silica gel chromatography using 0.5-2% methanol/dichloromethane gradient to afford 2-[1-(4-chlorobenzoyl)piperidin-4-ylmethoxy]-6-fluorobenzonitrile as an oil. (120 mg; 71% yield).
Workup
- customReaction
- customwas quenched with 2 mL 1 N HCl
- extractionMixture was extracted twice with 10 mL of ethyl acetate and organic layers
- washMixture was then washed with sat. NaHCO3, brine
- dry with materialdried over MgSO4
- filtrationMixture was filtered
- concentrationconcentrated to an oil
- customMaterial was purified via flash silica gel chromatography
Sources & evidence
- ORD record
- ord-d8ecdbc5805b4fa59ad99f32212c302e
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07985755B2
Reaction notes
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