N,N-Dimethyl-1,4-cyclohexanediamine → N,N-Dimethyl-N'-(3-pyridin-2-yl-7,8-dihydro-6H-cyclopenta[g]quinoxalin-2yl)-cyclohexane-1,4-diamine

HRID 1266138ノート

反応式

HRID 1266138 の反応式
Cl[C:2]1[C:3]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[N:4][C:5]2[CH:6]=[C:7]3[CH2:14][CH2:13][CH2:12][C:8]3=[CH:9][C:10]=2[N:11]=1.[CH3:21][N:22]([CH3:30])[CH:23]1[CH2:28][CH2:27][CH:26]([NH2:29])[CH2:25][CH2:24]1>C1(C)C=CC=CC=1>[CH3:21][N:22]([CH3:30])[CH:23]1[CH2:28][CH2:27][CH:26]([NH:29][C:2]2[C:3]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[N:4][C:5]3[CH:6]=[C:7]4[CH2:14][CH2:13][CH2:12][C:8]4=[CH:9][C:10]=3[N:11]=2)[CH2:25][CH2:24]1

参加物

4

反応物 2

HCID 345823N,N-Dimethyl-1,4-cyclohexanediamineHCID 185489952-chloro-3-pyridin-2-yl-7,8-dihydro-6H-cyclopenta[g]quinoxaline

生成物 1

HCID 18549022N,N-Dimethyl-N'-(3-pyridin-2-yl-7,8-dihydro-6H-cyclopenta[g]quinoxalin-2yl)-cyclohexane-1,4-diamine収率 43.6%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of 2-chloro-3-pyridin-2-yl-7,8-dihydro-6H-cyclopenta[g]quinoxaline (0.5 g) and N,N-dimethyl-cyclohexane-1,4-diamine (0.51 g) in toluene (30 mL) was refluxed under nitrogen atmosphere for 16 hours. The reaction was cooled, filtered, and concentrated under vacuum. The residue was purified by flash chromatography (silica gel, 1:19 methanol/dichloromethane) to give a yellow solid. Recrystallization from methanol and water gave the product as yellow crystals ( 0.3 g); mp 158-161° C.

後処理

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by flash chromatography (silica gel, 1:19 methanol/dichloromethane)
  5. customto give a yellow solid
  6. customRecrystallization from methanol and water

出典と根拠

ORDレコード
ord-9243754aa7994a89a3de227b87fa0525
出典データセット
uspto-grants-2003_04
特許番号
US06548499B1

反応ノート

読み込み中…