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

HRID 14111

Reaktionsgleichung

Reaktionsgleichung von HRID 14111
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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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]+.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-ecb8757435e74c26a364a25fc1369c41
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727997B2

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