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

HRID 1445461ノート

反応式

HRID 1445461 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 66611,3-Dimethyl-2-imidazolidinone溶媒

反応条件

温度
210 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fa959dc6df8d4df8a479af5a64d95c86
出典データセット
uspto-grants-2010_02
特許番号
US07666873B2

反応ノート

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