Imidazole → N-[2-(t-butyldiphenylsilyloxy)ethyl]aniline

HRID 2378544Notes

Reaction equation

HRID 2378544 reaction equation
[NH:1]([CH2:8][CH2:9][OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[Si:16](Cl)([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CN(C=O)C>[Si:16]([O:10][CH2:9][CH2:8][NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 31235N-(2-Hydroxyethyl)anilineHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 57245284N-[2-(t-butyldiphenylsilyloxy)ethyl]anilineYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2-anilinoethanol (5.82 g, TCI) in anhydrous DMF (50 ml) was added with imidazole (3.23 g, TCI), added dropwise with a solution of t-butyldiphenylsilyl chloride (12.48 g, TCI) in DMF (50 ml) under ice cooling, stirred for 30 minutes, then warmed to room temperature, and further stirred for 3.5 hours. The reaction mixture was added with water (100 ml), and extracted with ethyl acetate (100 ml). The organic layer was washed successively with water and saturated brine, and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=9:1) to obtain the title compound (Intermediate 46, 15.61 g).

Workup

  1. stirringfurther stirred for 3.5 hours
  2. extractionextracted with ethyl acetate (100 ml)
  3. washThe organic layer was washed successively with water and saturated brine
  4. customdried
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by flash column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-b975197e7d724dabb359a484134e866e
Source dataset
uspto-grants-2008_12
Patent number
US07470807B2

Reaction notes

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