Hydrochloric Acid → 2-Amino-1-[4-(benzyloxy)phenyl]ethan-1-one

HRID 1607731Notes

Reaction equation

HRID 1607731 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:18])[CH2:16]Cl)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N2CN3CN(C2)C[N:20]1C3.C(O)C.Cl>C(Cl)(Cl)Cl>[NH2:20][CH2:16][C:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:10][CH:11]=1)=[O:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 4101HexamethylenetetramineHCID 145794621-[4-(Benzyloxy)phenyl]-2-chloroethan-1-one

Product 1

HCID 145794632-Amino-1-[4-(benzyloxy)phenyl]ethan-1-oneYield 77%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

78 g of 1-(4-benzyloxyphenyl)-2-chloroethanone and 63 g of hexamine are dissolved in 2.2 liters of chloroform, and the mixture is stirred at room temperature overnight. The mixture is condensed to a volume of 1.1 liters, and refluxed for 3 hours. After cooling, the precipitated crystals are collected by filtration, washed and then dried. The colorless crystals thus obtained are added to a mixture of 750 ml of ethanol and 120 ml of conc. hydrochloric acid, and the mixture is refluxed for 50 minutes. After cooling, the precipitated crystals are collected by filteration, washed and then dried. 55.6 g of 2-amino-1-(4-benzyloxyphenyl)ethanone are obtained as colorless crystals.

Workup

  1. customcondensed to a volume of 1.1 liters
  2. temperaturerefluxed for 3 hours
  3. temperatureAfter cooling
  4. filtrationthe precipitated crystals are collected by filtration
  5. washwashed
  6. customdried
  7. customThe colorless crystals thus obtained
  8. temperaturethe mixture is refluxed for 50 minutes
  9. temperatureAfter cooling
  10. customthe precipitated crystals are collected by filteration
  11. washwashed
  12. customdried

Sources & evidence

ORD record
ord-8ef0ef01df664051a0f4909278860130
Source dataset
uspto-grants-1989_09
Patent number
US04866196

Reaction notes

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