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

HRID 1708350Notes

Reaction equation

HRID 1708350 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-1propanenitrile 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-70567050d3df4297a1a337bae8c2b83f
Source dataset
uspto-grants-1994_10
Patent number
US05358939

Reaction notes

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