Formaldehyde → Benzotriazol-1-ylmethyl-cyclohexylamine

HRID 1676504Notes

Reaction equation

HRID 1676504 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([NH2:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.[CH2:17]=O>CCOCC>[N:1]1([CH2:17][NH:16][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]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 7965CyclohexylamineHCID 178418385HCID 178418385, compound

Product 1

HCID 814555Benzotriazol-1-ylmethyl-cyclohexylamineYield 86.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 54 g (0.45 mole) benzotriazole and 51.5 mL (0.45 mole) of cyclohexylamine in 2000 mL of ether was added dropwise 36.5 mL (0.45 mole) of 37% aqueous formaldehyde. The reaction mixture was stirred at room temperature for 18 hours. The mixture was dried over calcium chloride, filtered and concentrated under reduced pressure. 200 mL of hexanes was added to the residue and the resulting solid collected by filtration, washed with 300 mL of hexane to give 90.0 g of benzotriazol-1-ylmethyl-cyclohexylamine as a white solid.

Workup

  1. dry with materialThe mixture was dried over calcium chloride
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. addition200 mL of hexanes was added to the residue
  5. filtrationthe resulting solid collected by filtration
  6. washwashed with 300 mL of hexane

Sources & evidence

ORD record
ord-ffac674a8a53478ab379c92c42aeafb1
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

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