Dimethylformamide → N-{2-(2-ethoxyphenoxy)ethyl}-3-(4-fluorophenoxy)propylamine hydrochloride

HRID 596305Notes

Reaction equation

HRID 596305 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.[CH2:13]([O:15][C:16]1[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=1[O:18][CH2:19][CH2:20][NH2:21])[CH3:14].C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=O>O>[ClH:1].[CH2:13]([O:15][C:16]1[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=1[O:18][CH2:19][CH2:20][NH:21][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[CH3:14]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 743911-(3-Chloropropoxy)-4-fluorobenzeneHCID 53030422-(2-Ethoxyphenoxy)ethylamine

Product 1

HCID 21451982N-{2-(2-ethoxyphenoxy)ethyl}-3-(4-fluorophenoxy)propylamine hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.9 g of 1-chloro-3-(4-fluorophenoxy)-propane, l.8 g of 2-(2-ethoxyphenoxy)ethylamine, 0.53 g of sodium carbonate and 60 ml of dimethylformamide was heated at 80°-90° C for 15 hours. After cooling, the reaction mixture was poured into water and extracted with benzene. The extract was washed with water and dried over sodium sulfate and evaporated under reduced pressure. The oily residue was dissolved in ether and treated with ethanolic hydrogen chloride under cooling. The precipitate was collected by filtration and dried to give N-{2-(2-ethoxyphenoxy)ethyl}-3-(4-fluorophenoxy)propylamine hydrochloride, M.P. 78°-82° C. Recrystallization from ethanol-benzene gave white crystals, M.P. 84°-86° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with benzene
  3. washThe extract was washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. dissolutionThe oily residue was dissolved in ether
  7. additiontreated with ethanolic hydrogen chloride
  8. temperatureunder cooling
  9. filtrationThe precipitate was collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-37fbbc9a11e1490786b08cabb9eb7699
Source dataset
uspto-grants-1977_03
Patent number
US04010280

Reaction notes

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