Imidazole → 5-Amino-2-(4-tert-butyldimethylsilyloxypiperidino)benzonitrile

HRID 1744529Notes

Reaction equation

HRID 1744529 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]2)=[C:6]([CH:9]=1)[C:7]#[N:8].[C:17]([Si:21](Cl)([CH2:24]C)[CH2:22]C)([CH3:20])([CH3:19])[CH3:18].N1C=CN=C1.C(=O)([O-])O.[Na+]>CN(C)C=O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH2:11][CH2:12][CH:13]([O:16][Si:21]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:24])[CH3:22])[CH2:14][CH2:15]2)=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 516892Sodium BicarbonateHCID 219423135-Amino-2-(4-hydroxypiperidin-1-yl)benzonitrileHCID 22228218Tert-butyl(chloro)diethylsilane

Product 1

HCID 222282225-Amino-2-(4-tert-butyldimethylsilyloxypiperidino)benzonitrileYield 75.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Amino-2-(4-hydroxypiperidino)benzonitrile (4.0 g), tert-butyldiethylsilyl chloride (3.0 g) and imidazole (1.6 g) were stirred in dimethylformamide (20 ml) at room temperature for 1 h. The reaction mixture was treated with aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. The residue was recrystallized from n-hexane to give the title compound (4.2 g), melting point: 88–90° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customafter which the solvent was evaporated under reduced pressure
  5. customThe residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-7298e0a646fe43e2b78b7ca4a631d47f
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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