Morpholine → HCID 13518760, compound

HRID 370446Notes

Reaction equation

HRID 370446 reaction equation
Cl[C:2]1[C:11]2[CH:10]3[CH2:12][CH:7]([CH2:8][CH2:9]3)[C:6]=2[C:5]2=[N:13][N:14]=[C:15]([CH3:16])[N:4]2[N:3]=1.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>>[CH3:16][C:15]1[N:4]2[N:3]=[C:2]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[C:11]3[CH:10]4[CH2:12][CH:7]([C:6]=3[C:5]2=[N:13][N:14]=1)[CH2:8][CH2:9]4

Participants

3

Reactant 2

HCID 8083MorpholineHCID 13518759HCID 13518759, compound

Product 1

HCID 13518760HCID 13518760, compoundYield 80.6%

Procedure

The 6-chloro-7,8,9,10-tetrahydro-3-methyl-7,10-methano(1,2,4)triazolo[3,4-a]phthalazine (4.5 grams, 0.019 mol) was mixed with 25 milliliters of morpholine and the mixture heated at boiling under reflux for eight hours. The reaction mixture was concentrated and partitioned between methylene chloride and water. The organic layer was collected, dried over sodium sulfate and evaporated to dryness to yield 4.4 grams (80.6% yield) of 7,8,9,10-tetrahydro-3-methyl-6-(4-morpholinyl)-7,10-methano(1,2,4)triazolo[3,4-a]phthalazine. After recrystallization from benzene-hexane the product was found to melt at 166°-168° C. Infrared analysis and nuclear magnetic resonance analysis confirmed the assigned structure, as did elemental analysis. Calculated for C15H19N5O: C, 63.14; H, 6.71; N, 24.55. Found: C, 63.20; H, 6.71; N, 24.32.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for eight hours
  3. concentrationThe reaction mixture was concentrated
  4. custompartitioned between methylene chloride and water
  5. customThe organic layer was collected
  6. dry with materialdried over sodium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-e9fef641e9da4e278919f1847736c033
Source dataset
uspto-grants-1985_07
Patent number
US04526890

Reaction notes

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