Methyl 4-Formylbenzoate → Methyl 4-((4-methylpiperazin-1-yl)methyl)benzoate

HRID 273290

反応式

HRID 273290 の反応式
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=O)=[CH:6][CH:5]=1.[CH3:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.[H][H]>CO.[Pt]>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:17]2[CH2:18][CH2:19][N:14]([CH3:13])[CH2:15][CH2:16]2)=[CH:6][CH:5]=1

参加物

6

反応物 3

HCID 15294Methyl 4-FormylbenzoateHCID 531671-MethylpiperazineHCID 178418361HCID 178418361、化合物2 回

生成物 1

HCID 782222Methyl 4-((4-methylpiperazin-1-yl)methyl)benzoate収率 85.2%

試薬・触媒・溶媒 2

HCID 23939Platinum触媒HCID 887Methanol溶媒

反応条件

温度
90 °C

実験手順

A solution of 4-formyl-benzoic acid methyl ester (10.0 g, 61 mmol) in methanol (100 ml) is treated sequentially with 1-methylpiperazine (6.7 g, 67 mmol) and platinum (5%) on sulfided carbon (0.5 g). The resulting solution is then heated at 90° C. and is subjected to a pressure of 5 bar of hydrogen for a period of 4 hrs until the hydrogen uptake is complete. The reaction mixture is cooled to room temperature and filtrated over a pad of Celite. The methanol is removed under reduced pressure and replaced with toluene (100 ml). The resulting organic solution is extracted with aqueous HCl (2N, 2×50 ml). The aqueous layer is treated with concentrated aqueous NaOH (30%) to set the pH to 12 and is back-extracted with toluene (2×50 ml). The combined organic layers are concentrated in vacuo to give 12.9 g (85%) of 4-(4-methyl-piperazin-1-ylmethyl)-benzoic acid methyl ester as a pale yellow oil which may be further purified by distillation under reduced pressure.

後処理

  1. temperatureThe reaction mixture is cooled to room temperature
  2. filtrationfiltrated over a pad of Celite
  3. customThe methanol is removed under reduced pressure
  4. extractionThe resulting organic solution is extracted with aqueous HCl (2N, 2×50 ml)
  5. additionThe aqueous layer is treated with concentrated aqueous NaOH (30%)
  6. extractionis back-extracted with toluene (2×50 ml)
  7. concentrationThe combined organic layers are concentrated in vacuo

出典と根拠

ORDレコード
ord-4d64d70ec9914c91a5508e52e4ab1be8
出典データセット
uspto-grants-2008_11
特許番号
US07456283B2

関連ノート

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