Water → 4-Pyridazinecarbonitrile, 3-((2-(4-morpholinyl)ethyl)amino)-6-phenyl-, dihydrochloride

HRID 1249356Notes

Reaction equation

HRID 1249356 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][C:7]=1[C:8]#[N:9].[NH2:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.O>C(O)CCC>[ClH:1].[ClH:1].[O:22]1[CH2:23][CH2:24][N:19]([CH2:18][CH2:17][NH:16][C:2]2[N:3]=[N:4][C:5]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:6][C:7]=2[C:8]#[N:9])[CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 962WaterHCID 4082852-MorpholinoethylamineHCID 6404487HCID 6404487, compound

Product 1

HCID 30232604-Pyridazinecarbonitrile, 3-((2-(4-morpholinyl)ethyl)amino)-6-phenyl-, dihydrochlorideYield 81.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

7.3 g of the chlorine compound of Example 18 are dissolved in 60 ml of normal butanol, and 8 g of N-(2-aminoethyl)-morpholine are added. The mixture is heated under reflux for 3 hours and then poured into 1000 ml of water. The organic phase is extracted with ether and the ether solution is then extracted with a 1N solution of sulphuric acid. The aqueous phase is separated off, rendered alkaline with sodium hydroxide and extracted with ether. The ether phase is dried over magnesium sulphate and the solvent is then evaporated off to dryness in vacuo. This gives a yellow solid. Yield 81.3%; melting point 138° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 3 hours
  3. extractionThe organic phase is extracted with ether
  4. extractionthe ether solution is then extracted with a 1N solution of sulphuric acid
  5. customThe aqueous phase is separated off
  6. extractionextracted with ether
  7. dry with materialThe ether phase is dried over magnesium sulphate
  8. customthe solvent is then evaporated off to dryness in vacuo
  9. customThis gives a yellow solid

Sources & evidence

ORD record
ord-ad55efd06a7942e38586ede1ba1dc52b
Source dataset
uspto-grants-1986_12
Patent number
US04631280

Reaction notes

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