Morpholine → HCID 12472015, compound

HRID 918060Notes

Reaction equation

HRID 918060 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH2:9][N:8]3[C:14]([C:17]([F:20])([F:19])[F:18])=[N:15][N:16]=[C:7]3[C:6]=2[CH:21]=1.[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:11][CH3:12])=[C:6]([C:7]2[N:8]([CH2:9][C:10](=[O:13])[N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)[C:14]([C:17]([F:20])([F:18])[F:19])=[N:15][N:16]=2)[CH:21]=1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 12279219HCID 12279219, compound

Product 1

HCID 12472015HCID 12472015, compound

Procedure

4.8 g. (0.0152 mole) of 10-chloro-7-methyl-3-(trifluoromethyl)-5H-s-triazolo[4,3-d][1,4]benzodiazepin-6(7H)-one from example 1a are dissolved in 40 ml. of morpholine and the resulting solution is refluxed for 3 days. The morpholine is removed under vacuum, 3N aqueous NaOH is added, and the mixture is extracted with benzene. The benzene solution is dried over Na2SO4, decanted from drying agent, and the solvent removed under vacuum to yield a gum. This gum is chromatographed on silica gel plates with chloroform/ethyl acetate, 6:4. The largest band is isolated, extracted with chloroform, the chloroform is evaporated, and the residue is recrystallized from ethanol to yield 3-[5-chloro-2-(methylamino)phenyl]-4-[2-oxo-2-(4-morpholinyl)ethyl]-5-(trifluoromethyl)-1,2,4-triazole; m.p. 152°-153°.

Workup

  1. customThe morpholine is removed under vacuum, 3N aqueous NaOH
  2. additionis added
  3. extractionthe mixture is extracted with benzene
  4. dry with materialThe benzene solution is dried over Na2SO4
  5. customdecanted
  6. customfrom drying agent
  7. customthe solvent removed under vacuum
  8. customto yield a gum
  9. customThis gum is chromatographed on silica gel plates with chloroform/ethyl acetate, 6:4
  10. customThe largest band is isolated
  11. extractionextracted with chloroform
  12. customthe chloroform is evaporated
  13. customthe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-738df7be2bda4531875abaa5158255bc
Source dataset
uspto-grants-1976_07
Patent number
US03969366

Reaction notes

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