Benzene → HCID 21451984, compound

HRID 596306Notes

Reaction equation

HRID 596306 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:9][C:10]1[CH:31]=[CH:30][CH:29]=[CH:28][C:11]=1[O:12][CH2:13][CH2:14][NH:15][CH2:16][CH2:17][C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)=O)[CH3:8].[OH2:32].C1C=CC=CC=1.[O:39]1CCCC1>>[C:11]([OH:12])(=[O:39])[C:10]([OH:9])=[O:32].[CH2:7]([O:9][C:10]1[CH:31]=[CH:30][CH:29]=[CH:28][C:11]=1[O:12][CH2:13][CH2:14][NH:15][CH2:16][CH2:17][CH2:18][NH:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)[CH3:8]

Participants

6

Reactant 5

HCID 241BenzeneHCID 962WaterHCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 21451997HCID 21451997, compound

Product 1

HCID 21451984HCID 21451984, compound

Procedure

To a mixture of 0.35 g of lithium aluminum hydride and 15 ml of tetrahydrofuran, there was added dropwise a solution of 2.05 g of 3-{2-(2-ethoxyphenoxy)ethylamino}-p-fluoropropionanilide in 20 ml of tetrahydrofuran. Then, the resulting mixture was refluxed for 3 hours. To the reaction mixture cooled in ice, there were gradually added water and benzene. The organic layer was separated, dried over sodium sulfate and evaporated under reduced pressure. The oily residue was dissolved in isopropanol, and a warm solution of 0.8 g of oxalic acid in 10 ml of isopropanol was added thereto. After cooling, the precipitate was collected by filtration and dried to give N-{2-(2-ethoxyphenoxy)ethyl}-3-(4-fluoroanilino)propylamine hydrogen oxalate, M.P. 193°-196° C (decomp.). Recrystallization from methanol gave white crystals, M.P. 218°-219° C (decomp.).

Workup

  1. temperatureThen, the resulting mixture was refluxed for 3 hours
  2. temperatureTo the reaction mixture cooled in ice
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. dissolutionThe oily residue was dissolved in isopropanol
  7. additiona warm solution of 0.8 g of oxalic acid in 10 ml of isopropanol was added
  8. temperatureAfter cooling
  9. filtrationthe precipitate was collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-49fa7b5a4cb4430c9f159a618fbfc638
Source dataset
uspto-grants-1977_03
Patent number
US04010280

Reaction notes

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