(R)-N,N-dimethyl-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propan-1-amine → (+-)-Duloxetine

HRID 2234231

반응식

HRID 2234231 반응식
C(O[K])(C)(C)C.[CH3:7][N:8]([CH2:10][CH2:11][C@@H:12]([O:18][C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1)[C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)C>CS(C)=O>[CH3:7][NH:8][CH2:10][CH2:11][CH:12]([O:18][C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1)[C:13]1[S:14][CH:15]=[CH:16][CH:17]=1

참가 물질

4

반응물 2

HCID 24739908(R)-N,N-dimethyl-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propan-1-amineHCID 178418922HCID 178418922, 화합물

생성물 1

HCID 122252(+-)-Duloxetine수율 84.4%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
110 °C

실험 절차

tBuOK (16.8 g) is added to a solution of (R)-N,N-dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine (31 g) in DMSO (100 ml), bubbled with a moderate stream of nitrogen, and the mixture is stirred and heated at 110° C. for 2 hours. After cooling down to lab temperature, the mixture is diluted with water (300 ml) and the racemic product is extracted with toluene. After evaporation, 25 g (84%) of (RS)-N-methyl-3-(naphthyloxy)-3-(2-thienyl)propylamine is obtained.

후처리

  1. custombubbled with a moderate stream of nitrogen
  2. temperatureAfter cooling down to lab temperature
  3. additionthe mixture is diluted with water (300 ml)
  4. extractionthe racemic product is extracted with toluene
  5. customAfter evaporation

출처 및 근거

ORD 기록
ord-b7337c332b4c441e833ec95572d2cdcd
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709662B2

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