Dimethylformamide → N-(1,1-dimethylethyl)-2-[2-[2-(1H-indol-4-yl)-ethenyl]-phenoxy]-ethanamine

HRID 1906193Notes

Reaction equation

HRID 1906193 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]=[CH:12][C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[CH:16][NH:17]2.CN(C)C=O.[C:27]([NH2:31])([CH3:30])([CH3:29])[CH3:28].C(=O)([O-])[O-].[K+].[K+]>O>[CH3:28][C:27]([NH:31][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]=[CH:12][C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[CH:16][NH:17]2)([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6385Tert-ButylamineHCID 11430Potassium CarbonateHCID 542356984-[2-[2-[(2-chloro)-ethoxy]-phenyl]-ethenyl]-1H-indole

Product 1

HCID 3062769N-(1,1-dimethylethyl)-2-[2-[2-(1H-indol-4-yl)-ethenyl]-phenoxy]-ethanamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1.65 g of the product of Step A, 20 ml of dimethylformamide, 15 ml of tert.-butylamine and 770 mg of potassium carbonate was heated for 4 hours at 120° C. and was then diluted with 100 ml of water. The mixture was extracted with ethyl acetate and the extracts were washed with water, dried, concentrated under reduced pressure at 50° C. The residue was chromatographed on silica (eluent: ethyl acetate-triethylamine 9-1) to obtain 1.7 g of N-(1,1-dimethylethyl)-2-[2-[2-(1H-indol-4-yl)-ethenyl]-phenoxy]-ethanamine (trans E).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe extracts were washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure at 50° C
  5. customThe residue was chromatographed on silica (eluent: ethyl acetate-triethylamine 9-1)

Sources & evidence

ORD record
ord-563367fb1ef24bacab3e024c83102e36
Source dataset
uspto-grants-1987_03
Patent number
US04650811

Reaction notes

Loading…