Water → 2-[3-[[2-(4-Chlorophenyl)-4-methylthiazol-5-yl]methoxy]piperidin-1-yl]benzaldehyde

HRID 602143Notes

Reaction equation

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

Participants

Conditions

Temperature: 130 °C

Procedure

3-[[2-(4-Chlorophenyl)-4-methylthiazol-5-yl]methoxy]piperidine (59.1 mg, 0.183 mmol) and 2-fluorobenzaldehyde (0.0984 mL, 0.915 mmol) were dissolved in dimethylsulfoxide (2 mL). To this solution, cesium carbonate (119 mg, 0.366 mmol) was added and the mixture was stirred at 130° C. for 3 hours. Subsequently, water was added and the mixture was extracted with ethyl acetate and the extracted washed with brine, followed by drying over magnesium sulfate and evaporation of the solvent. Purification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=20:1->5:1) gave 47.8 mg (61%) of the desired compound as a colorless oil.

Workup

extractionthe mixture was extracted with ethyl acetate
washthe extracted washed with brine
dry with materialby drying over magnesium sulfate and evaporation of the solvent
customPurification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=20:1->5:1)

Sources & evidence

ORD record: ord-1dc97ea5c79b4b67a21d3623a6c8e23e
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902367B2

Reaction notes

Loading…