Imidazole → HCID 69385721, compound

HRID 916844Notes

Reaction equation

HRID 916844 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:5]=[CH:6][CH:7]=1.N1C=CN=C1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>CN(C=O)C>[Si:18]([O:12][CH2:11][CH2:10][CH2:9][CH2:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[NH2:1])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 18388302HCID 18388302, compound

Product 1

HCID 69385721HCID 69385721, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the 4-(3-aminophenyl)butan-1-ol [Hua Hsueh Hsueh Pao 1964, 30, 166-75. CAN 61:47615] (3.66 g) in dry DMF (30 ml) was treated with imidazole (1.66 g) and tert-butyldimethylsilyl chloride (3.5 g). The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was concentrated in vacuo and the residue partitioned between sat. NH4Cl(aq) and ethyl acetate. The aqueous phase was extracted with EtOAc and the combined organic phase washed with water, dried (Na2SO4) and concentrated in vacuo. The residue was purified by chromatography (Biotage, Petroleum ether-EtOAc 9:1) to give the title compound. LCMS RT=3.89 min.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue partitioned between sat. NH4Cl(aq) and ethyl acetate
  3. extractionThe aqueous phase was extracted with EtOAc
  4. washthe combined organic phase washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography (Biotage, Petroleum ether-EtOAc 9:1)

Sources & evidence

ORD record
ord-51d7938fdbc548d8b81ab6582820ef76
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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