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Acetic Anhydride → 4-Acetyl-5-[(benzyloxy)methyl]-1-(4-fluorobenzyl)piperazin-2-one

HRID 2109846
ノート
印刷プレビュー

反応式

HRID 2109846 の反応式
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:12][N:11]1[CH2:13][C:14]([O:16]C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=1.B(F)(F)F.[CH3:31][CH2:32][O:33]CC.C(N(CC)CC)C.C(OC(=O)C)(=O)C>ClCCl.CN(C1C=CN=CC=1)C>[C:32]([N:11]1[CH:10]([CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:12][N:24]([CH2:23][C:22]2[CH:25]=[CH:26][C:19]([F:18])=[CH:20][CH:21]=2)[C:14](=[O:16])[CH2:13]1)(=[O:33])[CH3:31]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 7918Acetic AnhydrideHCID 8000Boron trifluoride etherateHCID 8471TriethylamineHCID 673264-FluorobenzylamineHCID 57634653Methyl {2-[(benzyloxy)methyl]aziridin-1-yl}acetate

生成物 1

HCID 576346344-Acetyl-5-[(benzyloxy)methyl]-1-(4-fluorobenzyl)piperazin-2-one

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

反応条件

温度
95 °C

実験手順

A mixture of methyl {2-[(benzyloxy)methyl]aziridin-1-yl}acetate (0.4 g, 1.7 mmol), 4-fluorobenzylamine (0.38 g, 3.3 mmol), and boron trifluoride etherate (50 μL) was heated in a sealed glass tube at 95° C. for 68 h (Bull. Chem. Soc. Jpn., 1986, 59, 321). The resulting mixture was dissolved in dichloromethane (50 mL), cooled to 0° C., and treated with a mixture of triethylamine (0.95 mL, 6.8 mmol), DMAP (21 mg, 0.17 mmol), and acetic anhydride (0.48 mL, 5.1 mmol). The mixture was stirred at room temperature overnight, and extracted successively with saturated aqueous solution of sodium bicarbonate, dilute aqueous HCl, and brine. The organic extract was dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with a mixture of 2% methanol in ethyl acetate. Collection and concentration of appropriate fractions provided the title piperazinone.

後処理

  1. temperaturecooled to 0° C.
  2. extractionextracted successively with saturated aqueous solution of sodium bicarbonate, dilute aqueous HCl, and brine
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. additionThe residue was subjected to column chromatography on silica gel eluting with a mixture of 2% methanol in ethyl acetate
  8. customCollection and concentration of appropriate fractions

出典と根拠

ORDレコード
ord-1c03894fc7fa49e5998dcee1d55d2404
出典データセット
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07517532B2

反応ノート

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