N-Methylbutylamine → Methyl 3-{[butyl(methyl)amino]methyl}-5-methylbenzoate

HRID 348903

反応式

HRID 348903 の反応式
O[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([CH3:13])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].CS(Cl)(=O)=O.[CH3:19][NH:20][CH2:21][CH2:22][CH2:23][CH3:24]>C(Cl)Cl>[CH2:21]([N:20]([CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([CH3:13])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])[CH3:19])[CH2:22][CH2:23][CH3:24]

参加物

5

反応物 3

HCID 8068N-MethylbutylamineHCID 31297Methanesulfonyl chlorideHCID 21086184Methyl 3-(hydroxymethyl)-5-methylbenzoate

生成物 1

HCID 21086167Methyl 3-{[butyl(methyl)amino]methyl}-5-methylbenzoate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To methyl 3-(hydroxymethyl)-5-methylbenzoate prepared by the method in EXAMPLE SP-177 (1.1 g, 6.1 mmol), in anhydrous methylene chloride (10 mL) is added methanesulfonyl chloride (663 μL, 8.6 mmol) at −30° C., and the reaction is warmed to 0° C. The reaction stirred 1 h, then filtered. The filtrate is added to N-methylbutylamine (2.1 mL, 18.3 mmol), and the reaction stirred at room temperature 16 h. The solution is concentrated under reduced pressure. Purification by flash chromatography affords the title compound in pure form. ESI MS m/z 250.2 [M+H]+.

後処理

  1. filtrationfiltered
  2. stirringthe reaction stirred at room temperature 16 h
  3. concentrationThe solution is concentrated under reduced pressure
  4. customPurification by flash chromatography

出典と根拠

ORDレコード
ord-11bad6c8ad854cd88d2ebe30d073bd0d
出典データセット
uspto-grants-2007_02
特許番号
US07176242B2

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