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

HRID 2099450Notes

Reaction equation

HRID 2099450 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 extracts 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 extracts 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-16916ad9232c4c12ad858e0467fe1418
Source dataset
uspto-grants-2009_08
Patent number
US07569566B2

Reaction notes

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