Sodium Chloride → 4-(4-Bromobenzylidene)-1-[(6-chlorobenzo[b]thien-2-yl)sulfonyl]piperidine

HRID 352793Notes

Reaction equation

[Br-].[Br:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:5][CH:4]=1.[H-].[Na+].[Cl:31][C:32]1[CH:33]=[CH:34][C:35]2[CH:39]=[C:38]([S:40]([N:43]3[CH2:48][CH2:47][C:46](=O)[CH2:45][CH2:44]3)(=[O:42])=[O:41])[S:37][C:36]=2[CH:50]=1.[Na+].[Cl-]>O1CCCC1.C(O)C.C(OCC)(=O)C>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([CH:7]=[C:46]2[CH2:47][CH2:48][N:43]([S:40]([C:38]3[S:37][C:36]4[CH:50]=[C:32]([Cl:31])[CH:33]=[CH:34][C:35]=4[CH:39]=3)(=[O:41])=[O:42])[CH2:44][CH2:45]2)=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 0 °C

Procedure

In a mixed solvent of tetrahydrofuran (10 ml) and ethanol (10 ml) was dissolved 4-bromobenzyl triphenylphosphonium bromide (512 mg). The resulting solution was cooled to 0° C., followed by the successive addition of sodium hydride (60% in oil, 40 mg) and 1-[(6-chlorobenzo[b]thien-2-yl)sulfonyl]piperidin-4-one (297 mg). The resulting mixture was stirred at room temperature for 16 hours and at 50° C. for 9 hours. Saturated aqueous NaCl solution and ethyl acetate were added to the reaction mixture to separate the same. The resulting organic layer was dried over anhydrous magnesium sulfate, the filtrate was concentrated and the residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=4:1), whereby the title compound (colorless powder, 133 mg) was obtained.

Workup

customto separate the same
dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
concentrationthe filtrate was concentrated
customthe residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=4:1), whereby the title compound (colorless powder, 133 mg)
customwas obtained

Sources & evidence

ORD record: ord-949ae94802f847f6afe43a91cbb0645e
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06747023B1

Reaction notes

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