Diethyl Ether → HCID 86740915, compound

HRID 746050Notes

Reaction equation

HRID 746050 reaction equation
[C:1]1([C:7]2([CH2:16][CH2:17][NH:18][CH3:19])[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20]([O-:23])([O-:22])=O.[K+].[K+].[CH2:26](Br)[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[I-].[K+].CC[O:39]CC>O.CN(C=O)C>[C:8]([OH:39])(=[O:9])/[CH:7]=[CH:16]/[C:20]([OH:23])=[O:22].[C:1]1([C:7]2([CH:16]([CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:17][NH:18][CH3:19])[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 5

HCID 3283Diethyl EtherHCID 4875Potassium IodideHCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 13656118HCID 13656118, compound

Product 1

HCID 86740915HCID 86740915, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4.0 g (15.8 mmole) 2-(3-phenyl-2,3-dihydrobenzofuran-3-yl)-N-methylethylamine, 6.9 g (50.0 mmole) anhydrous K2CO3, 2.35 ml (17.1 mmole) phenethyl bromide, 0.2 g potassium iodide and 40 ml DMF was warmed to 80° and maintained there for 2 hours. After cooling, the mixture was poured into 400 ml water and extracted with Et2O (3×250 ml). The combined organics were washed with saturated NaCl solution and dried over MgSO4. The crude product, obtained by filtration and evaporation, was converted to a fumarate salt in Et2O. This was recrystallized from CH3CN to give 2.5 g (33%) of solid, m.p. 135.5°-138°.

Workup

  1. temperaturewas warmed to 80°
  2. temperaturemaintained there for 2 hours
  3. temperatureAfter cooling
  4. extractionextracted with Et2O (3×250 ml)
  5. washThe combined organics were washed with saturated NaCl solution
  6. dry with materialdried over MgSO4
  7. customThe crude product, obtained by filtration and evaporation
  8. customThis was recrystallized from CH3CN

Sources & evidence

ORD record
ord-1b90ddbb31bd4daf8b9eb93be2daa66f
Source dataset
uspto-grants-1986_07
Patent number
US04602035

Reaction notes

Loading…