2,5-Hexanedione → N-(2,5-Dimethyl-1H-pyrrol-1-yl)-6-(piperidin-1-yl)pyridazin-3-amine

HRID 1390002Notes

Reaction equation

HRID 1390002 reaction equation
[NH:1]([C:3]1[N:4]=[N:5][C:6]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:7][CH:8]=1)[NH2:2].C([O-])(=O)C.[Na+].[CH3:20][C:21](=O)[CH2:22][CH2:23][C:24](=O)[CH3:25]>>[CH3:25][C:24]1[N:2]([NH:1][C:3]2[N:4]=[N:5][C:6]([N:9]3[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]3)=[CH:7][CH:8]=2)[C:21]([CH3:20])=[CH:22][CH:23]=1

Participants

4

Reactant 3

HCID 80352,5-HexanedioneHCID 517045Sodium AcetateHCID 13016463HCID 13016463, compound

Product 1

HCID 23275379N-(2,5-Dimethyl-1H-pyrrol-1-yl)-6-(piperidin-1-yl)pyridazin-3-amine

Conditions

Temperature
65 °C

Procedure

A mixture of 7.4 g (28 m moles) of 3-hydrazino-6-piperidino-pyridazine, 2.3 g of sodium acetate and 3.7 g 2,5-hexanedione is heated for two hours at 65° C. The solvent is evaporated off under vacuum and the solid residue is dissolved in water and neutralized with sodium hydroxide. The product is purified by chromatography through a silicagel column using as the eluent a mixture methanol-chloroform 2.5:97.5. The solid recovered by evaporation of the eluate is crystallized from ethyl acetate yielding 2 g (27%) of the product of the title which melts at 185°-187° C.

Workup

  1. customThe solvent is evaporated off under vacuum
  2. dissolutionthe solid residue is dissolved in water and neutralized with sodium hydroxide
  3. customThe product is purified by chromatography through a silicagel column
  4. customThe solid recovered by evaporation of the eluate
  5. customis crystallized from ethyl acetate yielding 2 g (27%) of the product of the title which melts at 185°-187° C.

Sources & evidence

ORD record
ord-b3240521a33b45789e079a91a55a5353
Source dataset
uspto-grants-1981_01
Patent number
US04247551

Reaction notes

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