Water → HCID 22248250, compound

HRID 606220Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

After dissolving 400 mg of 2-tert-butoxy-6-vinylpyridine and 601 mg of 4-(2-fluorophenoxymethyl)-4-hydroxypiperidine hydrochloride in 5 ml of N,N-dimethylformamide, 0.44 ml of N,N-diisopropylethylamine was added and the mixture was stirred for 24 hours at 100° C. Water was added to the reaction solution and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine in that order and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by NH silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (18 mg, 2% yield).

Workup

additionwas added
washThe organic layer was washed with water and saturated brine in that order
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified by NH silica gel column chromatography (solvent: n-hexane/ethyl acetate)

Sources & evidence

ORD record: ord-fca5aeb795a14644970d3e006794bfa1
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915274B2

Reaction notes

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