2-(4-Bromophenyl)-1-morpholinoethanone → 4-(4-Bromophenethyl)morpholine

HRID 931507노트

반응식

HRID 931507 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=O)=[CH:10][CH:9]=1>O1CCCC1>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:12][CH:13]=1

참가 물질

4

반응물 2

HCID 8758802-(4-Bromophenyl)-1-morpholinoethanoneHCID 21226445Aluminium lithium hydride

생성물 1

HCID 121778014-(4-Bromophenethyl)morpholine수율 97%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-30 °C

실험 절차

To a mixture of lithium aluminum hydride (3.35 g, 88.16 mmol, 2.00 equiv) in tetrahydrofuran (100 mL) maintained under nitrogen at −30° C. was added a solution of 2-(4-bromophenyl)-1-morpholinoethanone (12.5 g, 44.17 mmol, 1.00 equiv) in tetrahydrofuran (30 mL) dropwise with stirring. The reaction mixture was stirred at −30° C. for 30 min and then at room temperature for 2 h. The reaction was then quenched sequentially by the addition of 3.5 mL of water, 10 mL of 15% aqueous sodium hydroxide solution and 3.5 mL of water. The solid was removed by filtration. The filtrate was extracted with 1×150 mL of ethyl acetate. The organic layer was collected then washed with 2×30 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 11.5 g (97%) of 4-(4-bromophenethyl)morpholine as a white solid. LC-MS: (ES, m/z): 311 [M+CH3CN+H]+, 270 [M+H]+, 130, 102.

후처리

  1. stirringThe reaction mixture was stirred at −30° C. for 30 min
  2. customThe reaction was then quenched sequentially by the addition of 3.5 mL of water, 10 mL of 15% aqueous sodium hydroxide solution and 3.5 mL of water
  3. customThe solid was removed by filtration
  4. extractionThe filtrate was extracted with 1×150 mL of ethyl acetate
  5. customThe organic layer was collected
  6. washthen washed with 2×30 mL of brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-57c8634255404c72a3e299611635f8c7
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296732B2

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