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

HRID 2234231

反応式

HRID 2234231 の反応式
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

参加物

4

反応物 2

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

生成物 1

HCID 122252(+-)-Duloxetine収率 84.4%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b7337c332b4c441e833ec95572d2cdcd
出典データセット
uspto-grants-2010_05
特許番号
US07709662B2

関連ノート

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