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

HRID 353323

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>C(N)CCC.CCCCC.ClC1C=CC=CC=1>[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

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

customto yield a reddish solution
temperatureThe solution was cooled down to room temperature
customthe removal of succinimides
washThe precipitate was washed with pentane
customdried
customto give a yellow residue
customto give a yellow solution that
stirringwas stirred at room temperature for ˜5 minutes
customwas consumed

Sources & evidence

ORD record: ord-6bd3ee9d2695469e9d5b114ef71ea79d
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06750343B2

Linked notes

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