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

HRID 2109846
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HRID 2109846 반응식
[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]
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참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

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온도
95 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1c03894fc7fa49e5998dcee1d55d2404
출처 데이터셋
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07517532B2

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