Morpholine → HCID 57507186, compound

HRID 1931190Notes

Reaction equation

HRID 1931190 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)[N:3]=1.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>O1CCOCC1.O>[Cl:8][C:6]1[N:7]=[C:2]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[N:3]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)[N:5]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 57507185HCID 57507185, compound

Product 1

HCID 57507186HCID 57507186, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of (4,6-dichloro-1,3,5-triazin-2-yl)-(4-trifluoromethoxyphenyl)amine (XIII) (5.0 g, 15.3 mmol) in dioxane (25 mL) was added i-Pr2(Et)N (2.37 g, 18.3 mmol) and morpholine (1.60 g, 18.3 mmol), and the resulting mixture heated at 85° C. for 12 hours. The reaction mixture was cooled to ambient temperature, diluted with water and stirred for 1 h. The white precipitate was filtered and dried under vacuum to give (4-chloro-6-morpholin-4-yl-1,3,5-triazin-2-yl)-(4-trifluoromethoxyphenyl)amine (XIV) (5.63 g, 98% yield): GC/MS m/z 375 (M+); 1H NMR (CDCl3) δ 7.55 (d, J=3.7 Hz, 2H), 7.51 (bs, 1H), 7.25 (d, J=2.2 Hz, 2H), 3.74-3.87 (m, 8H).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. filtrationThe white precipitate was filtered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-9ddabb28b22f492fb60488fe20f1fb0d
Source dataset
uspto-grants-2012_05
Patent number
US08188273B2

Reaction notes

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