Formaldehyde → N-Cyclobutyl-1H-benzotriazole-1-methanamine

HRID 1676501Notes

Reaction equation

HRID 1676501 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.[CH:10]1([NH2:15])[CH2:14][CH2:13][CH2:12]C1.[CH2:16]=O>CCOCC>[N:1]1([CH2:16][NH:15][CH:10]2[CH2:12][CH2:13][CH2:14]2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 2906CyclopentylamineHCID 178418385HCID 178418385, compound

Product 1

HCID 86637494N-Cyclobutyl-1H-benzotriazole-1-methanamine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 28.6 g (0.24 mole) benzotriazole and 17.6 g (0.24 mole) of cyclopentylamine in 1000 mL of ether was added dropwise, 19.5 mL (0.24 mole) of 37% aqueous formaldehyde. The reaction mixture was stirred at room temperature under for 18 hours. The mixture was dried over calcium chloride, filtered and concentrated under reduced pressure. Hexanes was added to the residue, concentrated under reduced pressure to give the crude benzotriazol-1-ylmethyl-cyclobutyl-amine as an oil, which was used in the next without further purification.

Workup

  1. additionwas added dropwise
  2. dry with materialThe mixture was dried over calcium chloride
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. additionHexanes was added to the residue
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6c9233427cba49e189cce271d793703e
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

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