Water → (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(4-methoxybenzyl)piperazine

HRID 1375044ノート

反応式

HRID 1375044 の反応式
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11](CC2C=CC=CC=2)[CH2:10][C@H:9]1[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)=[O:7].O.C([O-])=O.[NH4+]>C(O)C.[Pd]>[F:38][C:2]([F:1])([F:37])[C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([C:33]([F:34])([F:35])[F:36])[CH:32]=1)[C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]1[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)=[O:7]

参加物

6

反応物 3

HCID 962WaterHCID 2723923Ammonium formateHCID 53698566(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(4-methoxybenzyl)-4-benzylpiperazine

生成物 1

HCID 54306763(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(4-methoxybenzyl)piperazine収率 78%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

反応条件

温度
60 °C

実験手順

To a solution of (2R)-1-[3,5-bis(trifluoromethyl)-benzoyl]-2-(4-methoxybenzyl)-4-benzylpiperazine (4.90 g) in ethanol (50 ml) were added water (5 ml), ammonium formate (1.44 g), and 10% palladium on activated carbon [50% wet] (0.49 g) under nitrogen atmosphere. The reaction mixture was heated at 60° C. with stirring for 2 hours. Insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. Ethyl acetate (40 ml) and water (40 ml) were added to the residue, and the organic layer was separated, washed with brine, and dried over magnesium sulfate. After removal of the solvent by evaporation, the resulting residue was purified by column chromatography on silica gel (70 g) using a mixed solvent of ethyl acetate and methanol (10:1). The fractions containing the objective compound were collected and evaporated under reduced pressure to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(4-methoxybenzyl)piperazine (3.18 g) as syrup.

後処理

  1. customInsoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionEthyl acetate (40 ml) and water (40 ml) were added to the residue
  4. customthe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. customAfter removal of the solvent
  8. customby evaporation
  9. customthe resulting residue was purified by column chromatography on silica gel (70 g)
  10. additionThe fractions containing the objective compound
  11. customwere collected
  12. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-65878ed94aa041098f8e16bb042b7254
出典データセット
uspto-grants-2007_01
特許番号
US07166598B2

反応ノート

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