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

HRID 1676514Notes

Reaction equation

HRID 1676514 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) of 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 under ice-cooled bath and the resulting solid was collected by filtration and washed with hexane dried to give 58.6 g of benzotriazol-1-ylmethyl-cyclopentyl-amine 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 under ice-
  5. temperaturecooled bath
  6. filtrationthe resulting solid was collected by filtration
  7. washwashed with hexane
  8. customdried

Sources & evidence

ORD record
ord-1b8d0c09900b4c8f9b7c46447f75fbdc
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

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