Formaldehyde → N-(benzotriazol-1-ylmethyl)cyclopentanamine

HRID 1676502Notes

Reaction equation

HRID 1676502 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][CH2:11]1.[CH2:16]=O>CCOCC>[N:1]1([CH2:16][NH:15][CH:10]2[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 2906CyclopentylamineHCID 178418385HCID 178418385, compound

Product 1

HCID 5235843N-(benzotriazol-1-ylmethyl)cyclopentanamineYield 90.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To the mixture of 36 g (0.3 mole) benzotriazole and 30 mL (0.3 mole) of cyclopentylamine in 1400 mL of ether was added dropwise 22 mL (0.3 mole) of 37% aqueous formaldehyde. The reaction mixture was stirred at room temperature overnight. The solution was dried over calcium chloride, filtered and concentrated under pressure. Hexane was added to the residue cooled in an ice bath and the resulting solid was collected by filtration washing with hexane and then dried to give 58.6 g of benzotriazol-1-ylmethyl-cyclopentylamine as a white solid.

Workup

  1. dry with materialThe solution was dried over calcium chloride
  2. filtrationfiltered
  3. concentrationconcentrated under pressure
  4. additionHexane was added to the residue
  5. temperaturecooled in an ice bath
  6. filtrationthe resulting solid was collected by filtration
  7. washwashing with hexane
  8. customdried

Sources & evidence

ORD record
ord-8e7777087605449c99f17a24f4b4211e
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

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