1H-1,2,4-Triazole-1-propanenitrile, alpha-butyl-alpha-phenyl- → 2-Phenyl-2-[(1,2,4-triazol-1-yl)methyl]-1-hexylamine

HRID 1656013Notes

Reaction equation

HRID 1656013 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:11]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH2:14][N:15]1[CH:19]=[N:18][CH:17]=[N:16]1)[C:12]#[N:13])[CH2:8][CH2:9][CH3:10]>CCOCC>[C:20]1([C:11]([CH2:14][N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:12][NH2:13])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 1553371H-1,2,4-Triazole-1-propanenitrile, alpha-butyl-alpha-phenyl-HCID 21226445Aluminium lithium hydride

Product 1

HCID 199569622-Phenyl-2-[(1,2,4-triazol-1-yl)methyl]-1-hexylamineYield 69.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 21 g (0.55 mole) of lithium aluminum hydride was charged 127 g (0.50 mole) alpha-butyl-alpha-phenyl-1H-1,2,4-triazole-1-propanenitrile in 2500 mL of dry ether over 2.5 hours with stirring under nitrogen. The reaction was stirred for an additional 5 hours after which GLC indicated the reaction was complete. The reaction was quenched with sodium sulfate, filtered and the organic phase separated. The aqueous phase was extracted with 1000 mL of ether. The organics were combined, washed with 3×1.5 liters of ice water, dried, filtered and concentrated without external heating and gave 88 g (69.2% yield) of a pale green oil.

Workup

  1. stirringThe reaction was stirred for an additional 5 hours after which GLC
  2. customThe reaction was quenched with sodium sulfate
  3. filtrationfiltered
  4. customthe organic phase separated
  5. extractionThe aqueous phase was extracted with 1000 mL of ether
  6. washwashed with 3×1.5 liters of ice water
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. temperaturewithout external heating

Sources & evidence

ORD record
ord-dee0eb136a65420496329f1fa190fb2c
Source dataset
uspto-grants-1993_10
Patent number
US05252594

Reaction notes

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