Benzoyl Peroxide → N-(Quinoxalin-6-ylmethyl)butan-1-amine

HRID 1266541Notes

Reaction equation

HRID 1266541 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[N:5]2.Br[N:13]1[C:17](=O)[CH2:16][CH2:15][C:14]1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.BrCC1C=C2C(=CC=1)N=CC=N2>ClC1C=CC=CC=1.C(N)CCC.CCCCC>[CH2:14]([NH:13][CH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[N:5]2)[CH2:15][CH2:16][CH3:17]

Participants

8

Reactant 4

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 2425676-MethylquinoxalineHCID 102145106-(Bromomethyl)quinoxaline2×

Product 1

HCID 12071593N-(Quinoxalin-6-ylmethyl)butan-1-amine

Reagents, catalysts & solvents 3

HCID 7964ChlorobenzeneSolventHCID 8003PentaneSolventHCID 8007ButylamineSolvent

Conditions

Temperature
85 °C

Procedure

In a 50 ml flask, 6-methyl-quinoxaline (1.25 g, 8.68 mmol) was dissolved together with N-bromosuccinimide (2.32 g, 13.0 mmol) and benzoyl-peroxide (0.15 g, 0.62 mmol) in 31 g of chlorobenzene. The solution was stirred with heating at 85° C for 2.0 hours to yield a reddish solution. The solution was cooled down to room temperature and one volume of pentane was added to facilitate the removal of succinimides. The precipitate was washed with pentane and the extracts were combined with the chlorobenzene solution. The yellow solution was vacuum dried to give a yellow residue mainly composed of 6-bromomethyl-quinoxaline. The yellow solid was dissolved in 19.0 g of n-butylamine to give a yellow solution that was stirred at room temperature for ˜5 minutes. Analysis of a sample showed that the 6-bromomethyl-quinoxaline was consumed to give exclusively 6-n-butylaminomethyl-quinoxaline as a deep yellow oil (1.71 g, 92% over all yield). MS (70 ev): 215 M+, 172 (M+—CH3—CH2—CH2), 143 (M+—CH3—CH2—CH2—CH2).

Workup

  1. customto yield a reddish solution
  2. temperatureThe solution was cooled down to room temperature
  3. customthe removal of succinimides
  4. washThe precipitate was washed with pentane
  5. customdried
  6. customto give a yellow residue
  7. customto give a yellow solution that
  8. stirringwas stirred at room temperature for ˜5 minutes
  9. customwas consumed

Sources & evidence

ORD record
ord-aa03f6113f204eeab18349edb04628a0
Source dataset
uspto-grants-2003_04
Patent number
US06548670B1

Reaction notes

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