Ethyl 4-bromobutyrate → Ethyl 4-[(2,5-dimethoxyphenyl)ethylamino]butanoate

HRID 475926ノート

反応式

HRID 475926 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH2:11][CH2:12][NH2:13].Br[CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].C(N(C(C)C)CC)(C)C>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH2:11][CH2:12][NH:13][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]

参加物

4

反応物 3

HCID 76300Ethyl 4-bromobutyrateHCID 766322,5-DimethoxyphenethylamineHCID 81531Diisopropylethylamine

生成物 1

HCID 67431306Ethyl 4-[(2,5-dimethoxyphenyl)ethylamino]butanoate収率 94%

実験手順

(2,5-Dimethoxyphenyl)ethylamine 3 (8.33 gm, 0.046 moles), ethyl 4-bromobutyrate (11.64 gm, 0.060 moles) and diisopropylethylamine (7.76 gm, 0.060 moles) were stirred at 110-120° C. for 18 hours, cooled, and partitioned between 50 ml DCM and 50 ml water. The aqueous layer was extracted thrice with 50 ml portions of DCM. The combined organic extracts were washed with saturated NaCl, dried over Na2SO4, filtered, and concentrated by rotary evaporation under reduced pressure. The crude product was purified by flash chromatography on silica gel, eluting with a gradient mixture of ethyl acetate and hexane. Ethyl 4-[(2,5-dimethoxyphenyl)ethylamino]butanoate 4 (12.73 gm, 94% yield) was isolated after removing the solvent. 1H NMR (CDCl3) δ 6.44-6.78, 3H, m; 4.11, 2H, q; 3.79, 3H, s; 3.76, 3H, s; 3.08-3.19, 4H, m; 2.30, 2H, t; 1.79, 2H, m; 1.24, 3H, t; 1.03, 3H, t.

後処理

  1. temperaturecooled
  2. custompartitioned between 50 ml DCM and 50 ml water
  3. extractionThe aqueous layer was extracted thrice with 50 ml portions of DCM
  4. washThe combined organic extracts were washed with saturated NaCl
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation under reduced pressure
  8. customThe crude product was purified by flash chromatography on silica gel
  9. washeluting with a gradient mixture of ethyl acetate and hexane

出典と根拠

ORDレコード
ord-b4ef648e398445ccaff645288501344c
出典データセット
uspto-grants-2014_01
特許番号
US08637658B2

反応ノート

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