Hydrochloric Acid → 2-(2-Methoxyphenoxy)ethyl amine

HRID 505320Notes

Reaction equation

HRID 505320 reaction equation
Cl.C(OC(=O)[NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19])(C)(C)C>O1CCOCC1.C(OCC)(=O)C>[CH3:19][O:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[O:11][CH2:10][CH2:9][NH2:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18537920HCID 18537920, compound

Product 1

HCID 17130052-(2-Methoxyphenoxy)ethyl amine

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Under an atmosphere of Nitrogen, 3N HCl (3 ml) was added to a solution of [2-(2-methoxy-phenoxy)-ethyl]-carbamic acid tert-butyl ester (320 mg, 1.20 mmol) in dioxane (3 ml). The mixture was heated to reflux (2 h). Upon cooling, the reaction mixture was taken up in ethyl acetate, and extracted several times with H2O. The combined H2O extracts were then made alkaline by addition of NaOH 2N, and extracted with ethyl acetate. The ethyl acetate extract was dried (Na2SO4), and the solvent was evaporated. The obtained product (180 mg, 90%) was used in the next step without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux (2 h)
  3. temperatureUpon cooling
  4. extractionextracted several times with H2O
  5. additionby addition of NaOH 2N
  6. extractionextracted with ethyl acetate
  7. extractionThe ethyl acetate extract
  8. dry with materialwas dried (Na2SO4)
  9. customthe solvent was evaporated
  10. customThe obtained product (180 mg, 90%) was used in the next step without further purification

Sources & evidence

ORD record
ord-c8b3fae136de4693b2333f18cb92b5d6
Source dataset
uspto-grants-2010_08
Patent number
US07781441B2

Reaction notes

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