Water → Agomelatine Impurity 2

HRID 1978008ノート

反応式

HRID 1978008 の反応式
[NH2:1][CH2:2][CH:3]=[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[CH2:7][CH2:6][CH2:5]1.C(N(CC)CC)C.[C:23](Cl)(=[O:25])[CH3:24].O>C1COCC1>[C:23]([NH:1][CH2:2]/[CH:3]=[C:4]1\[CH2:5][CH2:6][CH2:7][C:8]2[C:13]\1=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)(=[O:25])[CH3:24]

参加物

6

反応物 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 54094556HCID 54094556、化合物

生成物 1

HCID 15523935Agomelatine Impurity 2収率 40.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1-(2-aminoethylidene)-7-methoxy-1,2,3,4-tetrahydronaphthalene (2.0 g, 9.74 mmol) and triethylamine (1.5 g, 14,6 mmol) in THF (20 ml) was gradually added dropwise, under ice-cooling, acetyl chloride (0.76 g, 9.74 mmol). The mixture was stirred for 30 minutes at room temperature. The reaction mixture was poured into water, and the organic layer was subjected to extraction with chloroform. The extract solution was washed with brine and water, which was dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure. The residue was purified by means of a silica gel column chromatography (ethyl acetate), followed by recrystallization from ethyl acetate/hexane to give the above-titled compound (yield 0.96 g, 40%).

後処理

  1. temperaturecooling
  2. extractionthe organic layer was subjected to extraction with chloroform
  3. washThe extract solution was washed with brine and water, which
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. distillationThe solvent was then distilled off under reduced pressure
  6. customThe residue was purified by means of a silica gel column chromatography (ethyl acetate)
  7. customfollowed by recrystallization from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-198b743818f048838415d033a55e8fda
出典データセット
uspto-grants-2001_05
特許番号
US06235789B1

反応ノート

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