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

HRID 650924

반응식

HRID 650924 반응식
[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

참가 물질

7

반응물 4

HCID 260Hydrogen Bromide2회HCID 14798Sodium HydroxideHCID 2865472-(4-Methylpiperazin-1-yl)anilineHCID 23668193Sodium Nitrite

생성물 1

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

시약·촉매·용매 2

HCID 24611Copper bromide (CuBr2)촉매HCID 962Water용매

반응 조건

온도
22.5 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-72b8e0e9ba1f4bc2b2f3968847ee08fd
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06277852B1

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