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

HRID 353323

反応式

HRID 353323 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 7964Chlorobenzene溶媒HCID 8003Pentane溶媒HCID 8007Butylamine溶媒

反応条件

温度
85 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6bd3ee9d2695469e9d5b114ef71ea79d
出典データセット
uspto-grants-2004_06
特許番号
US06750343B2

関連ノート

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