Sodium Hydroxide → [3-(5-Methoxy-benzofuran-2-yl)-3-phenyl-propyl]-methyl-amine

HRID 250195

Reaction equation

HRID 250195 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][CH:9]=[CH:8][C:7]=2[CH:11]=1.[CH3:12][N:13](C(=O)C(F)(F)F)[CH2:14][CH2:15][CH:16](OC(=O)C(F)(F)F)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:15][CH2:14][NH:13][CH3:12])=[CH:8][C:7]=2[CH:11]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 259435-MethoxybenzofuranHCID 58088435HCID 58088435, compound

Product 1

HCID 11623507[3-(5-Methoxy-benzofuran-2-yl)-3-phenyl-propyl]-methyl-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

5-methoxybenzofuran (0.48 g) and trifluoro-acetic acid 3-[methyl-(2,2,2-trifluoro-acetyl)-amino]-1-phenyl-propyl ester (0.48 g) were mixed and heated in a sealed tube at 110° C. for 90 minutes. Upon cooling, the reaction mixture was taken up in methanol and treated with excess 1N sodium hydroxide solution, sufficient to form a strongly basic solution. After stirring for 20 minutes, the reaction mixture was concentrated at reduced pressure to remove the bulk of the methanol. The resulting mixture was partitioned between ethyl acetate and water. The layers were separated and the organic layer was evaporated to dryness. Purification by column chromatography (silica gel, dichloromethane (130):methanol (10):ammonium hydroxide (1)) followed by preparative tlc afforded [3-(5-Methoxy-benzofuran-2-yl)-3-phenyl-propyl]-methyl-amine (M+H=296) as the major component.

Workup

  1. temperatureUpon cooling
  2. customsufficient to form a strongly basic solution
  3. concentrationthe reaction mixture was concentrated at reduced pressure
  4. customto remove the bulk of the methanol
  5. customThe resulting mixture was partitioned between ethyl acetate and water
  6. customThe layers were separated
  7. customthe organic layer was evaporated to dryness
  8. customPurification by column chromatography (silica gel, dichloromethane (130):methanol (10):ammonium hydroxide (1))

Sources & evidence

ORD record
ord-8bfd3924d9a14e69914d03f9d7cc7dba
Source dataset
uspto-grants-2011_01
Patent number
US07863305B2

Linked notes

Loading…