3-(1-Benzoylpiperidin-4-yl)-6-fluorobenzo[b]thiophene-2-carboxylic acid → (4-(6-Fluorobenzo[b]thiophen-3-yl)piperidin-1-yl)phenylmethanone

HRID 1784722Notes

Reaction equation

[C:1]([N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[C:16]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:17]=3[S:18][C:19]=2C(O)=O)[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>N1C2C(=CC=CC=2)C=CC=1>[F:27][C:24]1[CH:25]=[CH:26][C:16]2[C:15]([CH:12]3[CH2:13][CH2:14][N:9]([C:1]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[O:8])[CH2:10][CH2:11]3)=[CH:19][S:18][C:17]=2[CH:23]=1

Participants

Conditions

Temperature: 200 °C

Procedure

3-(1-Benzoylpiperidin-4-yl)-6-fluorobenzo[b]thiophene-2-carboxylic acid (10 g, 26 mmol) was suspended in quinoline (100 mL) and cupper powder (0.5 g) was added. After stirring at 200° C. for 1 h, the mixture was cooled to room temperature and partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulfate and evaporated. The obtained residue was purified by silica gel column chromatography eluting hexane/ethyl acetate to give (4-(6-fluorobenzo[b]thiophen-3-yl)piperidin-1-yl)phenylmethanone (5.0 g, 48%) as yellow crystals.

Workup

temperaturethe mixture was cooled to room temperature
custompartitioned between ethyl acetate and water
dry with materialThe organic layer was dried over magnesium sulfate
customevaporated
customThe obtained residue was purified by silica gel column chromatography
washeluting hexane/ethyl acetate

Sources & evidence

ORD record: ord-81940f2bc5ad4c58a4fb7712597babf4
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504411B2

Reaction notes

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