Benzenamine, 4-(4-morpholinyl)- → HCID 21916463, compound

HRID 1246241Notes

Reaction equation

HRID 1246241 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[F:14][C:15]([F:27])([F:26])[O:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]=[O:25])=[CH:19][CH:18]=1>C(Cl)Cl>[N:4]1([C:7]2[CH:13]=[CH:12][C:10]([NH:11][C:24]([NH:23][C:20]3[CH:21]=[CH:22][C:17]([O:16][C:15]([F:14])([F:26])[F:27])=[CH:18][CH:19]=3)=[O:25])=[CH:9][CH:8]=2)[CH2:3][CH2:2][O:1][CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 92298p-(Trifluoromethoxy)phenyl isocyanate

Product 1

HCID 21916463HCID 21916463, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-morpholinoaniline (270 mg, 1.5 mmol) in dry methylene chloride is added 4-trifluoromethoxy-phenyl isocyanate (229 μl, 1.5 mmol) at room temperature. After stirring at room temperature for 2 hours, the solvent is removed by rotary evaporator. The crude product, 1-(4-Morpholin-4-yl-phenyl)-3-(4-trifluoromethoxy-phenyl)-urea, is recrystallized in methanol to give a white solid (424 mg, 74% yield); 1H NMR (400 MHz, d-DMSO) δ3.00 (dd, J=4.7, 4.8 Hz, 4H), 3.71 (dd, J=4.5, 4.9 Hz, 4H), 6.87 (d, J=9.0 Hz, 2H), 7.24 (d, 2H), 7.29 (d, 2H), 7.5 (m, 2H), 8.44 (s, 1H), 8.75 (s, 1H); MS (ES+) m/e 382.1 (M+H+).

Workup

  1. customthe solvent is removed by rotary evaporator
  2. customThe crude product, 1-(4-Morpholin-4-yl-phenyl)-3-(4-trifluoromethoxy-phenyl)-urea, is recrystallized in methanol

Sources & evidence

ORD record
ord-d7909cb0b2824fae9fd55d4babc60da5
Source dataset
uspto-grants-2006_10
Patent number
US07125997B2

Reaction notes

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