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

HRID 2211090Notes

Reaction equation

HRID 2211090 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 hydride2×

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 a 5 liter flask stirring under nitrogen, fitted with a mechanical stirrer, was charged 21 g (0.55 mole) of lithium aluminum hydride. To the 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. 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. customfitted with a mechanical stirrer
  2. stirringThe reaction was stirred for an additional 5 hours after which GLC
  3. customThe reaction was quenched with sodium sulfate
  4. filtrationfiltered
  5. customthe organic phase separated
  6. extractionThe aqueous phase was extracted with 1000 mL of ether
  7. washwashed with 3×1.5 liters of ice water
  8. customdried
  9. filtrationfiltered
  10. concentrationconcentrated
  11. temperaturewithout external heating

Sources & evidence

ORD record
ord-896ac414ad2047ea8641fdea26b154f4
Source dataset
uspto-grants-1995_10
Patent number
US05462931

Reaction notes

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