Reaktion #46779

Reaktionsgleichung

amine

2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethylamine

2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethylamine

mesitylenesulfonyl chloride

→

title compounds

Ausbeute 67.0%

2,4,6-Trimethyl-N-[2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethyl]benzenesulfonamide

Ausbeute 67.0%

Lösungsmittel

HCl

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was cooled
2. 2
   Extraktionextracted with three 7 mL portions of ethyl acetate
3. 3
   WaschenThe combined organic layers were washed with three 5 mL portions of 1 N aqueous HCl, 5 mL of brine, three 5 mL portions of saturated aqueous sodium bicarbonate
4. 4
   Trocknendried over magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated in vacuo
7. 7
   Sonstigeto afford 62 mg (82.1%) of crude solid
8. 8
   Sonstigechromatographed on silica gel
9. 9
   SonstigeThe material from the column was crystallized from ether-hexanes

Vorschrift

A mixture of 42 mg (0.18 mmol) of 2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethylamine and 45 mg, 0.21 mmol) of mesitylenesulfonyl chloride in 0.5 mL of pyridine was warmed to 45° C. The reaction was monitored by thin layer chromatography (ethyl acetate-hexanes (3:7)) indicating a new less polar product compared to the amine. After 6 hours, the mixture was cooled and diluted with 7 mL of 1 N aqueous HCl and extracted with three 7 mL portions of ethyl acetate. The combined organic layers were washed with three 5 mL portions of 1 N aqueous HCl, 5 mL of brine, three 5 mL portions of saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 62 mg (82.1%) of crude solid. The crude material was adsorbed onto silica gel and chromatographed on silica gel using dichloromethane-hexanes (gradient: 50%-100%). The material from the column was crystallized from ether-hexanes to afford 52 mg (67%) of the title compounds as a white solid, m.p. 189° C.-191° C.; MS: m/z 409.15 (M−).

Quelle