Ethanolamine → HCID 59341474、化合物

HRID 15245

反応式

HRID 15245 の反応式
[CH2:1]([C:8]([N:20]([CH3:22])[CH3:21])([CH2:18][CH3:19])[C:9]([C:11]1[CH:16]=[CH:15][C:14](F)=[CH:13][CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([CH2:25][NH2:26])[OH:24].C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O.O>[CH2:1]([C:8]([N:20]([CH3:22])[CH3:21])([CH2:18][CH3:19])[C:9]([C:11]1[CH:16]=[CH:15][C:14]([NH:26][CH2:25][CH2:23][OH:24])=[CH:13][CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 700EthanolamineHCID 11430Potassium CarbonateHCID 193605992-Benzyl-2-(dimethylamino)-1-(4-fluorophenyl)butan-1-one

生成物 1

HCID 59341474HCID 59341474、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
140 °C

実験手順

44.9 g (0.15 mol) 2-Benzyl-1-(4-fluorophenyl)-2-dimethylamino-1-butanone and 61.08 g (1.05 mol) ethanolamine are dissolved in 400 ml dimethylacetamide. 41.5 (0.3 mol) Potassium carbonate are added and the suspension is heated to 140° C. while stirring. The reaction mixture is kept at this temperature during 16 hours, cooled to room temperature and diluted with water. The aqueous phase is several times extracted with ethyl acetate, the combined organic extracts washed with water and dried over magnesium sulfate. Evaporation of the solvent gives the crude product as a yellowish-brown oil. The product is purified by chromatography on silica gel (eluent: petroleum ether/ethyl acetate 2:1→1:1). The fractions containing the product are collected to give a slightly yellowish solid product. Recrystallisation from ethyl acetate/hexane gave 2-benzyl-1-[4-(2-hydroxyethylamino)phenyl]-2-dimethylamino-1-butanone as slightly yellowish crystals melting at 109-111° C. Yield: 34.7 g (68%). 1H-NMR data are in agreement with the proposed structure.

後処理

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washthe combined organic extracts washed with water
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent
  6. customgives the crude product as a yellowish-brown oil
  7. customThe product is purified by chromatography on silica gel (eluent: petroleum ether/ethyl acetate 2:1→1:1)
  8. additionThe fractions containing the product
  9. customare collected
  10. customto give a slightly yellowish solid product
  11. customRecrystallisation from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-3d5c76a6ecfa4060aa28c6ae79dff7db
出典データセット
uspto-grants-2010_06
特許番号
US07732504B2

関連ノート

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