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

HRID 14111

반응식

HRID 14111 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

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]+.

후처리

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

출처 및 근거

ORD 기록
ord-ecb8757435e74c26a364a25fc1369c41
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727997B2

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