Hydrogen Bromide → 1-(2-Bromophenyl)-4-methylpiperazine

HRID 650924

反応式

HRID 650924 の反応式
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2N)[CH2:4][CH2:3]1.N([O-])=O.[Na+].[OH-].[Na+].[BrH:21]>O.[Cu](Br)Br>[Br:21][C:9]1[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=1[N:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1

参加物

7

反応物 4

HCID 260Hydrogen Bromide2 回HCID 14798Sodium HydroxideHCID 2865472-(4-Methylpiperazin-1-yl)anilineHCID 23668193Sodium Nitrite

生成物 1

HCID 120694321-(2-Bromophenyl)-4-methylpiperazine

試薬・触媒・溶媒 2

HCID 24611Copper bromide (CuBr2)触媒HCID 962Water溶媒

反応条件

温度
22.5 °C

実験手順

A solution of 2-(4-methylpiperazin-1-yl)-aniline (23.77 grams, 0.124 mol) in 80 mL of 48% hydrobromic acid was cooled to 20° C. and treated with a solution of sodium nitrite (8.6 grams, 0.124 mol) in 35 mL of water while maintaining a temperature of 20-25° C. To this was added a solution of copper (II) bromide (3.5 grams, 0.024 mol) in 12 mL of 48% HBr. The mixture was heated to 85° C. for approximately 30 minutes, poured over crushed ice in a large beaker and neutralized with dilute aqueous sodium hydroxide. The crude product was extracted into diethyl ether and concentrated in vacuo to a black oil which was chromatographed on silica gel using triethylamine:methanol:methylene chloride (0.5:10:90) as the eluent. The product, 1-bromo-2-(4-methylpiperazin-1-yl)benzene, was obtained as a brown oil, 20 grams. Mass spectrum: 254 (M+), 256. 1H-NMR (CDCl3, 300 MHz) δ7.55 (1H, d), 7.30 (1H, t), 7.05 (1H, d), 6.9 (1H, t), 3.05 (4H, br s), 2.55 (4H, t), 2.35 (3H, s).

後処理

  1. temperatureThe mixture was heated to 85° C. for approximately 30 minutes
  2. additionpoured
  3. customover crushed ice in a large beaker
  4. extractionThe crude product was extracted into diethyl ether
  5. concentrationconcentrated in vacuo to a black oil which
  6. customwas chromatographed on silica gel

出典と根拠

ORDレコード
ord-72b8e0e9ba1f4bc2b2f3968847ee08fd
出典データセット
uspto-grants-2001_08
特許番号
US06277852B1

関連ノート

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