Diethyl Ether → 1-Phenethylamine

HRID 483000Notes

Reaction equation

HRID 483000 reaction equation
C(OCC)(=O)C.[CH3:7][C@H:8]([NH2:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(OCC)C>C(Cl)(Cl)Cl>[CH3:7][CH:8]([NH2:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 8857Ethyl Acetate2×HCID 758181-Phenethylamine, (-)-

Product 1

HCID 74081-Phenethylamine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The mother liquors from above were acidified with 167 ml. 1N hydrochloric acid, extracted with 5×125 ml. ethyl acetate, the extracts combined, washed with brine, dried (MgSO4) and the solvent evaporated to obtain 49 g. of residue. This was dissolved in 350 ml. warm ethyl acetate, 22.4 g. l-(-)-alpha-methylbenzylamine added and the solution cooled to room temperature. Ethyl ether, 350 ml. was added and the mixture refrigerated overnight. The precipitated solid was collected by filtration, washed with cold ether and dried in vacuo to obtain 44.0 g. of salt. This was dissolved in 880 ml. ethyl acetate and set aside at room temperature for six hours. Filtration gave 12.4 g., M.P. 139°-140° C. After standing overnight, the mother liquor afforded a second crop, 11.66 g., M.P. 139°-140° C. The optical rotation (in chloroform) for the first crop was [alpha]D -30.9°, and [alpha]D -26.6° for the second crop.

Workup

  1. extraction1N hydrochloric acid, extracted with 5×125 ml
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent evaporated
  5. customto obtain 49 g
  6. dissolutionThis was dissolved in 350 ml
  7. additionwas added
  8. customthe mixture refrigerated overnight
  9. filtrationThe precipitated solid was collected by filtration
  10. washwashed with cold ether
  11. customdried in vacuo
  12. customto obtain 44.0 g
  13. dissolutionThis was dissolved in 880 ml
  14. filtrationFiltration
  15. customgave 12.4 g
  16. customthe mother liquor afforded a second crop, 11.66 g
  17. customwas [alpha]D -30.9°
  18. custom[alpha]D -26.6°

Sources & evidence

ORD record
ord-cfbe63cda73d47f685d7cc867f83a4bd
Source dataset
uspto-grants-1986_03
Patent number
US04576964

Reaction notes

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