Hydrochloric Acid → 3-Morpholino-5-(trifluoromethyl)aniline

HRID 1375604Notes

Reaction equation

HRID 1375604 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]([NH:17]C(=O)OC(C)(C)C)[CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl>C(O)(C)C>[N:1]1([C:7]2[CH:12]=[C:11]([C:13]([F:15])([F:14])[F:16])[CH:10]=[C:9]([NH2:17])[CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86606802(3-Morpholin-4-yl-5-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester

Product 1

HCID 185432013-Morpholino-5-(trifluoromethyl)aniline

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

[3-(4-morpholinyl)-5-(trifluoromethyl)phenyl]-carbamic acid, 1,1-dimethylethyl ester (Example 90b; 1.7 g, 5 mmol) is treated with a solution of hydrogen chloride in isopropanol (30 mL of 4 M) and heated at 60° C. for 5 h. The solvent is evaporated off under reduced pressure and the residue is treated with aqueous sodium hydrogen carbonate solution (80 mL) and extracted with ethyl acetate (3×80 mL). The combined extacts are washed with brine (2×50 mL), dried (MgSO4) and the solvent is evaporated off under reduced pressure to give the crude product which is purified by recrystallisation from ether-hexane to afford the title compound as yellow crystalline solid, m.p. 96–97° C.

Workup

  1. customThe solvent is evaporated off under reduced pressure
  2. additionthe residue is treated with aqueous sodium hydrogen carbonate solution (80 mL)
  3. extractionextracted with ethyl acetate (3×80 mL)
  4. washThe combined extacts are washed with brine (2×50 mL)
  5. dry with materialdried (MgSO4)
  6. customthe solvent is evaporated off under reduced pressure
  7. customto give the crude product which
  8. customis purified by recrystallisation from ether-hexane

Sources & evidence

ORD record
ord-de26100a820c471a99016e285a36d7f9
Source dataset
uspto-grants-2007_01
Patent number
US07169791B2

Reaction notes

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