반응 #42421

반응 방정식

methanesulfonyl chloride

methyl 3-(hydroxymethyl)-5-methylbenzoate

Butylamine

triethylamine

→

title compound

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

용매

methylene chloride

methylene chloride

반응 조건

후처리

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

실험 절차

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).

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