Benzylamine → HCID 23347165, compound

HRID 1855959Notes

Reaction equation

HRID 1855959 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH2:14]Br)[CH2:7][OH:8])[CH3:2].[CH2:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(OCC)(=O)C>CC(C)=O>[CH2:16]([NH:23][CH2:14][CH2:13][O:12][C:11]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][C:4]=1[O:3][CH2:1][CH3:2])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 8857Ethyl AcetateHCID 543733553-Ethoxy-4-(2-bromoethoxy)benzyl alcohol

Product 1

HCID 23347165HCID 23347165, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 27.5 g of 3-ethoxy-4-(2-bromoethoxy)benzyl alcohol and 53.5 g of benzylamine was heated to 130°-135° C. for 1.5 hours with stirring. After cooling the reaction mixture, 300 ml of ethyl acetate was added therein and the mixture was washed twice each time with 50 ml of water, dried with anhydrous sodium sulfate and distilled under reduced pressure to provide an orange oily product. To the product was added 50 ml of acetone to form crystals, which were recovered by filtration under suction to provide 22.5 g of N-benzyl-2-(2-ethoxy-4-hydroxymethylphenoxy)ethylamine having a melting point of 164°-167° C.

Workup

  1. temperaturewas heated to 130°-135° C. for 1.5 hours
  2. additionwas added
  3. washthe mixture was washed twice each time with 50 ml of water
  4. dry with materialdried with anhydrous sodium sulfate
  5. distillationdistilled under reduced pressure
  6. customto provide an orange oily product
  7. customto form crystals, which
  8. filtrationwere recovered by filtration under suction

Sources & evidence

ORD record
ord-5c7d3d64f88c419b8bca76ac44892cca
Source dataset
uspto-grants-1980_08
Patent number
US04217305

Reaction notes

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