Dibenzylamine → HCID 563365, compound

HRID 1880820Notes

Reaction equation

HRID 1880820 reaction equation
[N:1]1([CH2:10]O)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.[CH2:12]([NH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1C2C=CC=CC=2N=N1>CCO>[CH2:20]([N:19]([CH2:10][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7656DibenzylamineHCID 2241691H-Benzotriazole-1-methanolHCID 178418385HCID 178418385, compound

Product 1

HCID 563365HCID 563365, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1H-Benzotriazole-1-methanol (51.0 g, 0.342 mol) was weighed into a round bottom flask and solubilized in EtOH (800 mL). Dibenzylamine (67.5 g, 0.342 mol) was added slowly (over 5 min) to the rapidly stirred solution. Formation of a white precipitate was observed shortly after starting addition. The solution was abandoned to stir for 24 h. At this time the reaction is judged complete by NMR (product fragments on LCMS to show only benzotriazole). The majority of the solvent was removed by rotovap and diethyl ether (1 L) was added to the residue with vigorous stirring. This mixture was filtered, the filtrand washed with ether and dried under vacuum to yield the desired product as a fluffy white solid (112 g, quat. yield). 1H NMR (400 MHz, chloroform-d) δ ppm 3.80 (s, 4 H) 5.48 (s, 2 H) 7.21 (d, J=8.34 Hz, 1 H) 7.34-7.43 (m, 11 H) 7.49 (d, 1 H) 8.09 (d, J=7.83 Hz, 1 H).

Workup

  1. additionaddition
  2. customThe majority of the solvent was removed by rotovap and diethyl ether (1 L)
  3. additionwas added to the residue with vigorous stirring
  4. filtrationThis mixture was filtered
  5. washthe filtrand washed with ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-ba4868ec508b41aea98ce0e3a6eed9bc
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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