Methyl iodide → 3-(4-Bromo-phenyl)-1-methyl-piperazine

HRID 1802776ノート

反応式

HRID 1802776 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][NH:12][CH2:11][CH2:10][NH:9]2)=[CH:4][CH:3]=1.[CH2:14](N(CC)CC)C.CI.[Cl-].[NH4+]>CC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[NH:9][CH2:10][CH2:11][N:12]([CH3:14])[CH2:13]2)=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 218386862-(4-Bromophenyl)piperazine

生成物 1

HCID 578992273-(4-Bromo-phenyl)-1-methyl-piperazine収率 46.3%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒2 回

反応条件

温度
0 °C

実験手順

To a cooled (0° C.) solution of 2-(4-bromophenyl)piperazine (4.07 g, 16.0 mmol) and triethylamine (17 mL, 122 mmol) in acetone (50 mL) was added a solution of methyl iodide (1.4 mL, 22 mmol) in acetone (20 mL) over 50 min and the reaction mixture was stirred at 0° C. for 15 minutes, warmed to room temperature, and stirred for 16 h. The reaction mixture was slowly treated with saturated ammonium chloride (150 mL) and extracted with ethyl acetate (200 mL×3). The organic layers were combined, dried over magnesium sulfate, filtered and concentrated in vacuo. Purification via flash silica gel column chromatography (heptane/ethyl acetate) gave 3-(4-bromo-phenyl)-1-methyl-piperazine (1.89 g, 46% yield). LCMS (m/z): 257.00 (M+1).

後処理

  1. temperaturewarmed to room temperature
  2. stirringstirred for 16 h
  3. extractionextracted with ethyl acetate (200 mL×3)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification via flash silica gel column chromatography (heptane/ethyl acetate)

出典と根拠

ORDレコード
ord-7be4b9ce46754c03853998d73cba79e3
出典データセット
uspto-grants-2013_01
特許番号
US08349883B2

反応ノート

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