Tert-Butylamine → 1-[4-{-2-(1,1-Dimethylethylamino)-ethoxy}-phenyl]-ethanone

HRID 1721950

Reaction equation

HRID 1721950 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:13])[CH3:12])=[CH:7][CH:6]=1.[C:14]([NH2:18])([CH3:17])([CH3:16])[CH3:15]>O>[CH3:15][C:14]([NH:18][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:13])[CH3:12])=[CH:7][CH:6]=1)([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 136911911-[4-(2-Chloroethoxy)phenyl]ethanone

Product 1

HCID 136911921-[4-{-2-(1,1-Dimethylethylamino)-ethoxy}-phenyl]-ethanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 6.5 g of the product of Step A in 30 ml of tert.-butylamine was heated at 120° C. for 30 hours and was then diluted with water and extracted with ethyl acetate. The organic phase was washed with water, dried over a deshydrant, filtered and evaporated to dryness. The residue was chromatographed over silica and eluted with a 9-1 ethyl acetate-triethylamine mixture to obtain 7.264 g of 1-[4-{-2-(1,1-dimethylethylamino)-ethoxy}-phenyl]-ethanone.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water
  3. customdried over a deshydrant
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was chromatographed over silica
  7. washeluted with a 9-1 ethyl acetate-triethylamine mixture

Sources & evidence

ORD record
ord-fca304eb29c24e84bbfaa78ddfa3439e
Source dataset
uspto-grants-1989_08
Patent number
US04853408

Linked notes

Loading…