Water → Agomelatine Impurity 2

HRID 1978008노트

반응식

HRID 1978008 반응식
[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]

참가 물질

6

반응물 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 54094556HCID 54094556, 화합물

생성물 1

HCID 15523935Agomelatine Impurity 2수율 40.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-198b743818f048838415d033a55e8fda
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06235789B1

반응 노트

불러오는 중…