Water → HCID 86615888, compound

HRID 602213Notes

Reaction equation

HRID 602213 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][O:21][CH:22]3[CH2:27][CH2:26][CH2:25][NH:24][CH2:23]3)=[CH:16][CH:15]=2)=[CH:10][CH:9]=1.F[C:29]1[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=1[CH:31]=[O:32].O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][O:21][CH:22]3[CH2:27][CH2:26][CH2:25][N:24]([C:36]4[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=4)[CH:31]=[O:32])[CH2:23]3)=[CH:16][CH:15]=2)=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67970o-FluorobenzaldehydeHCID 589926553-[(4′-Chloro[1,1′-biphenyl]-4-yl)methoxy]piperidine

Product 1

HCID 86615888HCID 86615888, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Tetrabutylammonium iodide (26.9 mg, 0.0729 mmol) and potassium carbonate (206 mg, 1.46 mmol) were added to a solution of 3-[(4′-chlorobiphenyl-4-yl)methoxy]piperidine (220 mg, 0.729 mmol) and 2-fluorobenzaldehyde (0.159 mL, 1.46 mmol) in N,N-dimethylformamide (5 mL). The mixture was stirred at 100° C. for 8 hours. Subsequently, water was added and the mixture was extracted with ethyl acetate and washed with brine. The washed product was dried over magnesium sulfate and the solvent was evaporated. Purification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=40:1->10:1) gave 156 mg (53%) of the desired compound as a pale yellow powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialThe washed product was dried over magnesium sulfate
  4. customthe solvent was evaporated
  5. customPurification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=40:1->10:1)

Sources & evidence

ORD record
ord-aa0b40b1bb7545c387930c3dda8f5de9
Source dataset
uspto-grants-2011_03
Patent number
US07902367B2

Reaction notes

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