Tert-Butylamine → HCID 20030191, compound

HRID 1721946Notes

Reaction equation

HRID 1721946 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[O:14])[CH3:13].[C:15]([NH2:19])([CH3:18])([CH3:17])[CH3:16].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH3:16][C:15]([NH:19][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[O:14])[CH3:13])([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 6385Tert-ButylamineHCID 11430Potassium CarbonateHCID 23036317HCID 23036317, compound

Product 1

HCID 20030191HCID 20030191, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2.58 g of the product of Step A, 8.3 ml of tert.-butylamine and 2.17 g of potassium carbonate in 7 ml of N,N-dimethylformamide was heated with stirring at 120° C. for 19 hours and was then diluted with water. The mixture was extracted with ethyl acetate and the organic phase was washed with water, dried over a deshydrant and evaporated to dryness under reduced pressure. The residue was chromatographed over silica and eluted with a 9-1 ethyl acetate-triethylamine mixture to obtain 2.571 g of 1-[2-{3-(1,1-dimethylethylamino)-propoxy}-phenyl]-ethanone.

Workup

  1. temperaturewas heated
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic phase was washed with water
  4. customdried over a deshydrant
  5. customevaporated to dryness under reduced pressure
  6. customThe residue was chromatographed over silica
  7. washeluted with a 9-1 ethyl acetate-triethylamine mixture

Sources & evidence

ORD record
ord-32d0d4aa0bea45f2a972c5fb1428edb9
Source dataset
uspto-grants-1989_08
Patent number
US04853408

Reaction notes

Loading…