Reaktion #42421

Reaktionsgleichung

methanesulfonyl chloride

methyl 3-(hydroxymethyl)-5-methylbenzoate

Butylamine

triethylamine

→

title compound

Methyl 3-[(butylamino)methyl]-5-methylbenzoate

Lösungsmittel

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered
2. 2
   workup.STIRRINGthe reaction mixture is stirred at room temperature for 5 h
3. 3
   Waschenwashed with 1 N hydrochloric acid, and saturated sodium bicarbonate
4. 4
   Trocknendried (magnesium sulfate)
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   SonstigePurification by flash column chromatography (silica, 89:10:1 chloroform/methanol/ammonium hydroxide)

Vorschrift

To an ice-cold, stirred solution of methyl 3-(hydroxymethyl)-5-methylbenzoate (200 mg, 1.1 mmol) in methylene chloride (2.2 mL) is added triethylamine (0.304 mL, 2.2 mmol) followed by methanesulfonyl chloride (0.116 mL, 1.5 mmol). The reaction mixture is stirred for 15 min and filtered. Butylamine (0.543 mL, 5.5 mmol) is added to the filtrate, and the reaction mixture is stirred at room temperature for 5 h. The reaction mixture is diluted with methylene chloride (10 mL), washed with 1 N hydrochloric acid, and saturated sodium bicarbonate, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 89:10:1 chloroform/methanol/ammonium hydroxide) provides the title compound. 1H NMR (300 MHz, CDCl3) δ 7.75 (s, 1H), 7.70 (s, 1H), 7.24 (br s, 1H), 4.42 (d, J=9 Hz, 2H), 3.90 (s, 3H), 3.16 (m, 2H), 2.38 (s, 3H), 1.64 (s, 2H), 1.44 (m, 9H), 1.27 (m, 2H), 0.89 (t, J=7 Hz, 3H).

Quelle