(3S,4R)-3-[(1,3-Benzodioxol-5-yloxy)methyl]-1-benzyl-4-(4-fluorophenyl)piperidine → Paroxetine

HRID 431263

反応式

HRID 431263 の反応式
C([N:8]1[CH2:13][CH2:12][C@@H:11]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C@H:10]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]3[O:29][CH2:30][O:31][C:25]=3[CH:24]=2)[CH2:9]1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[CH:15]1[C:14]([C@H:11]2[C@H:10]([CH2:21][O:22][C:23]3[CH:28]=[CH:27][C:26]4[O:29][CH2:30][O:31][C:25]=4[CH:24]=3)[CH2:9][NH:8][CH2:13][CH2:12]2)=[CH:19][CH:18]=[C:17]([F:20])[CH:16]=1

参加物

5

反応物 2

HCID 9953865(3S,4R)-3-[(1,3-Benzodioxol-5-yloxy)methyl]-1-benzyl-4-(4-fluorophenyl)piperidineHCID 178418361HCID 178418361、化合物

生成物 1

HCID 43815Paroxetine収率 98.7%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A solution containing 8.4 g (0.02 mol) of (−)trans-1-benzyl-4-(4-fluorophenyl)-3-(3,4-methylenedioxyphenoxymethyl)piperidine in 120 ml of ethanol is hydrogenated in an autoclave in the presence of 0.6 g of 10% palladium-on-carbon catalyst at 30 to 40° C. under 2×105 Pa pressure for 2 to 3 hours. After taking up the hydrogen, the catalyst is filtered under nitrogen gas and the filtrate is evaporated to solvent-free to give 6.5 g of paroxetine base as evaporation residue in the form of a colourless oil. The product is suspended in 80 ml of water and after adding 2 ml of glacial acetic acid, it is stirred until dissolution. Then, the solution of 2 g of ammonium chloride in 10 ml of water is added to the mixture. After stirring for 4 hours, the precipitated crystalline title product is filtered at 10° C., twice washed with 10 ml of cold water each and dried on air to obtain 6,5 g (89%) of title compound, m.p.: 136-138° C.; [α]D20−86.6° (c=1, methanol).

後処理

  1. filtrationthe catalyst is filtered under nitrogen gas
  2. customthe filtrate is evaporated to solvent-free

出典と根拠

ORDレコード
ord-b2d885b987ec46acb85558efcd4c9c3e
出典データセット
uspto-grants-2003_12
特許番号
US06657062B1

関連ノート

読み込み中…