Morpholine → 1,4-Dimorpholino-7-phenylpyrido(3,4-d)pyridazine

HRID 1604903Notes

Reaction equation

HRID 1604903 reaction equation
CS[C:3]1[N:8]=[N:7][C:6](SC)=[C:5]2[CH:11]=[N:12][C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:14][C:4]=12.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>>[O:24]1[CH2:25][CH2:26][N:21]([C:3]2[N:8]=[N:7][C:6]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[C:5]3[CH:11]=[N:12][C:13]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[CH:14][C:4]=23)[CH2:22][CH2:23]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 12246673HCID 12246673, compound

Product 1

HCID 1004941,4-Dimorpholino-7-phenylpyrido(3,4-d)pyridazine

Conditions

Temperature
180 °C

Procedure

1 part by weight of 1,4-dimethylmercapto-7-phenylpyrido[3,4-d]pyridazine and 10 parts by volume of morpholine are placed in a glass tube, and the glass tube is sealed. The reaction system is heated at 180°C for 8 hours. The excess amount of morpholine is removed by evaporating under reduced pressure, and water is added to the residue. Thus precipitated crude crystals are collected by filtration. The crude crystals are adsorbed on a column packed with silica-gel, followed by eluting with a mixture of acetone and benzene (1:4). The eluate is concentrated under reduced pressure and recrystallized from methanol to obtain 1,4-dimorpholino-7-phenylpyrido[3,4-d]pyridazine as pale yellow needles melting at 186° to 188°C.

Workup

  1. customthe glass tube is sealed
  2. customThe excess amount of morpholine is removed
  3. customby evaporating under reduced pressure, and water
  4. additionis added to the residue
  5. customThus precipitated crude crystals
  6. filtrationare collected by filtration
  7. washby eluting with a mixture of acetone and benzene (1:4)
  8. concentrationThe eluate is concentrated under reduced pressure
  9. customrecrystallized from methanol

Sources & evidence

ORD record
ord-c11001a614ff4854af63ac55490459ef
Source dataset
uspto-grants-1976_04
Patent number
US03948908

Reaction notes

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