Ethyl Acetate → 4-[(2S,5R)-4-benzyl-2,5-dimethylpiperazin-1-yl]-2-methylbenzonitrile

HRID 1593373노트

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HRID 1593373 반응식
[CH2:1]([N:8]1[CH2:13][C@H:12]([CH3:14])[NH:11][CH2:10][C@H:9]1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([CH3:25])[CH:18]=1.C(N(C(C)C)CC)(C)C.C(OCC)(=O)C>CN1C(=O)N(C)CC1>[CH2:1]([N:8]1[C@H:9]([CH3:15])[CH2:10][N:11]([C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([CH3:25])[CH:18]=2)[C@@H:12]([CH3:14])[CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 38260554-Fluoro-2-methylbenzonitrileHCID 10632028(2R,5S)-1-benzyl-2,5-dimethylpiperazine

생성물 1

HCID 686953104-[(2S,5R)-4-benzyl-2,5-dimethylpiperazin-1-yl]-2-methylbenzonitrile수율 25.2%

시약·촉매·용매 1

HCID 66611,3-Dimethyl-2-imidazolidinone용매

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온도
210 °C

실험 절차

To a solution of 3.81 g of (2R,5S)-1-benzyl-2,5-dimethylpiperazine in 20 ml of DMI were added 3.80 g of 4-fluoro-2-methylbenzonitrile and 7.27 g of diisopropylethylamine, followed by 2 days of stirring in a sealed tube at 210° C. After the addition of ethyl acetate to the reaction solution, the mixture was washed with water and the organic layer was dried over anhydrous sodium sulfate. The solvent was removed by evaporation and the resulting residue was purified by silica gel column chromatography to obtain 1.50 g of the title compound as a solid from an eluate eluted with hexane-ethyl acetate (85:15, v/v).

후처리

  1. washthe mixture was washed with water
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. customThe solvent was removed by evaporation
  4. customthe resulting residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-d986939cf1b44accb77e2103c0777add
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07297698B2

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