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

HRID 1802776노트

반응식

HRID 1802776 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매2회

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-7be4b9ce46754c03853998d73cba79e3
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349883B2

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