Potassium Carbonate → 2-(4-Benzyl-1-(5-methoxy-2-nitrophenyl)piperazin-2-yl)acetic acid

HRID 80494

反応式

HRID 80494 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH:10]([CH2:14][C:15]([O:17]C)=[O:16])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[C:20]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=1[N+:28]([O-:30])=[O:29].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>C(#N)C.O>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:20]2[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=2[N+:28]([O-:30])=[O:29])[CH:10]([CH2:14][C:15]([OH:17])=[O:16])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 5656543-Fluoro-4-nitroanisoleHCID 156654662-Piperazineacetic acid, 4-(phenylmethyl)-, methyl ester

生成物 1

HCID 667698072-(4-Benzyl-1-(5-methoxy-2-nitrophenyl)piperazin-2-yl)acetic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
90 °C

実験手順

To a solution of Example 12C (0.907 g, 3.65 mmol) in acetonitrile (11.69 mL) was added 2-fluoro-4-methoxy-1-nitrobenzene (0.50 g, 2.92 mmol) and potassium carbonate (2.019 g, 14.61 mmol) in water (2.92 mL) followed by 18-crown-6 (0.039 g, 0.146 mmol), and the mixture was heated with an oil bath at 90° C. (reflux) for 24 hours. The solvent was evaporated and water was added followed by dichloromethane. The water phase was washed three times with dichloromethane to remove starting material and then acidified with 1N HCl until pH=1. The acid product was extracted three times with dichloromethane, dried quickly with sodium sulfate and concentrated to give the title compound. MS (ESI) m/z 386.1 (M+H)+.

後処理

  1. temperature(reflux) for 24 hours
  2. customThe solvent was evaporated
  3. additionwater was added
  4. washThe water phase was washed three times with dichloromethane
  5. customto remove
  6. extractionThe acid product was extracted three times with dichloromethane
  7. dry with materialdried quickly with sodium sulfate
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-1a25bfed7a854408a47cbd41ae7cce3d
出典データセット
uspto-grants-2014_09
特許番号
US08846663B2

関連ノート

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