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

HRID 353323

반응식

HRID 353323 반응식
[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]

참가 물질

8

반응물 4

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 2425676-MethylquinoxalineHCID 102145106-(Bromomethyl)quinoxaline2회

생성물 1

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

시약·촉매·용매 3

HCID 7964Chlorobenzene용매HCID 8003Pentane용매HCID 8007Butylamine용매

반응 조건

온도
85 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6bd3ee9d2695469e9d5b114ef71ea79d
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06750343B2

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