1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one → HCID 13685988, compound

HRID 1380520Notes

Reaction equation

HRID 1380520 reaction equation
[NH2:1][C:2]1[NH:3][C:4]([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:9][CH2:8]2)=[N:5][N:6]=1.CN(C)[CH:22]=[CH:23][C:24]([C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)=O>C(O)(=O)C>[CH2:13]([N:10]1[CH2:11][CH2:12][N:7]([C:4]2[N:3]=[C:2]3[N:1]=[CH:22][CH:23]=[C:24]([C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)[N:6]3[N:5]=2)[CH2:8][CH2:9]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 5670331-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-oneHCID 178509160HCID 178509160, compound

Product 1

HCID 13685988HCID 13685988, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2.58 g of (1-(5-amino-4H-1,2,4-triazol-3-yl)-4-benzylpiperazine and 1.76 g of 3-dimethylamino-1-(3-pyridyl)-2-propen-1-one (U.S. Pat. No. 4,281,000, Example 1) in 35 ml of glacial acetic acid was refluxed for 12 hours. The solution was taken to dryness in vacuo. The residue was partitioned between saturated sodium bicarbonate and dichloromethane (1:2). The dichloromethane layer was separated, dried over anhydrous sodium sulfate and filtered through a short column of magnesium silicate. The effluent was refluxed on a steam bath with the gradual addition of hexane until turbidity was noted. After cooling the precipitate was collected by filtration. The solid was recrystallized from dichloromethane/hexane and gave 2.20 g of the desired product as pale yellow crystals, mp 149°-150° C.

Workup

  1. customThe residue was partitioned between saturated sodium bicarbonate and dichloromethane (1:2)
  2. customThe dichloromethane layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered through a short column of magnesium silicate
  5. temperatureThe effluent was refluxed on a steam bath with the gradual addition of hexane until turbidity
  6. temperatureAfter cooling the precipitate
  7. filtrationwas collected by filtration
  8. customThe solid was recrystallized from dichloromethane/hexane

Sources & evidence

ORD record
ord-8492dbb6f2854ed08103ae0c0ccd5d2e
Source dataset
uspto-grants-1986_04
Patent number
US04582833

Reaction notes

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