Dimethylformamide → N-[1-methyl-5-[[3-[3-(1-piperidinylmethyl)phenoxy]propyl]amino]-1H-1,2,4-triazol-3-yl]formamide

HRID 2285526Notes

Reaction equation

HRID 2285526 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:8]([NH:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[CH:15]=2)=[N:7][C:6]([NH2:27])=[N:5]1.CN(C)[CH:30]=[O:31]>>[CH3:3][N:4]1[C:8]([NH:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[CH:15]=2)=[N:7][C:6]([NH:27][CH:30]=[O:31])=[N:5]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 71988Lamtidine

Product 1

HCID 20544845N-[1-methyl-5-[[3-[3-(1-piperidinylmethyl)phenoxy]propyl]amino]-1H-1,2,4-triazol-3-yl]formamide

Procedure

A mixture of sodium hydride (0.72 g) and 1-methyl-N5 -[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine (3.44 g) in dimethylformamide (50 ml) was heated under reflux for 8 h. The reaction mixture was cooled, poured onto water (300 ml) and extracted with ether. Evaporation of the organic extract gave a yellow oil, which was extracted with boiling cyclohexane (500 ml). As the cyclohexane extract was cooled a brown oil precipitated out. This oil was discarded and the supernatant solution was cooled to room temperature to give the title compound which was recrystallised from a mixture of ethyl acetate and light petroleum (b.p. 60°-80°) as a pale yellow solid (0.35 g) m.p. 68°-75° (decomposition). tlc, System C: Rf 0.6.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 8 h
  3. temperatureThe reaction mixture was cooled
  4. additionpoured onto water (300 ml)
  5. extractionextracted with ether
  6. customEvaporation of the
  7. extractionorganic extract
  8. customgave a yellow oil, which
  9. extractionwas extracted with boiling cyclohexane (500 ml)
  10. extractionAs the cyclohexane extract
  11. temperaturewas cooled a brown oil
  12. customprecipitated out

Sources & evidence

ORD record
ord-343320c4c7064eb5924c98ac5aaaf961
Source dataset
uspto-grants-1982_04
Patent number
US04323566

Reaction notes

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