Water → HCID 23508492, compound

HRID 1883681Notes

Reaction equation

HRID 1883681 reaction equation
[Si]([O:8][C:9]1[CH:30]=[CH:29][C:12]([CH2:13][N:14]([C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[OH:8][C:9]1[CH:30]=[CH:29][C:12]([CH2:13][N:14]([C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 23508429HCID 23508429, compound

Product 1

HCID 23508492HCID 23508492, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Then, 31 mg of 4-[N-[4-(tert-butyldimethylsilyloxy)benzyl]-N-(4-pyridyl)amino]benzonitrile was dissolved in 0.33 ml of tetrahydrofuran, and 0.15 ml of a 1 M tetrahydrofuran solution of tetrabutyl-ammonium fluoride was added thereto, followed by stirring at room temperature for 45 minutes. After water was added to the reaction mixture, the product was extracted with tetrahydrofuran-diethyl ether (1:1). After the extract was washed with water and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The resulting crude product was purified by TLC (using a 9:1 mixture of chloroform and methanol as the developing solvent) to obtain 14 mg of 4-[N-(4-hydroxybenzyl)-N-(4-pyridyl)amino]benzonitrile.

Workup

  1. extractionthe product was extracted with tetrahydrofuran-diethyl ether (1:1)
  2. washAfter the extract was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting crude product was purified by TLC (
  6. additiona 9:1 mixture of chloroform and methanol as the developing solvent)

Sources & evidence

ORD record
ord-93d16dbd8c5f4c0ba7a33a6407349c51
Source dataset
uspto-grants-2004_07
Patent number
US06762205B1

Reaction notes

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