تفاعل #5703

معادلة التفاعل

acetyl chloride

α-[3-(trifluoromethyl)benzylamino]-1-benzylindole-3-acetic acid

NaHCO3

NaHCO3

HCl

→

title compound

Methyl α-[3-(trifluoromethyl)benzylamino]-1-benzylindole-3-acetate

المذيبات

methanol

ظروف التفاعل

المعالجة

1. 1
   أخرىformed a dark
2. 2
   workup.STIRRINGAfter stirring for 22 hours the reaction mixture
3. 3
   استخلاصextracted twice with ether
4. 4
   غسيلThe combined organic extracts were washed with saturated NaHCO3 (1×75 mL), saturated brine (1×100 mL)
5. 5
   تجفيفdried with anhydrous NaSO4
6. 6
   تركيزconcentrated in vacuo

الإجراء التجريبي

To a magnetically stirred solution of 100 ml of methanol cooled in an ice-acetone bath at ca. -15° C., was treated dropwise with acetyl chloride (27.3 g, 350 mmol, 35 eq) over a six-minute period as a convenient way to generate HCl in situ. The solution was stirred at ambient temperature for 45 minutes, then solid α-[3-(trifluoromethyl)benzylamino]-1-benzylindole-3-acetic acid was added which formed a dark rose colored solution. After stirring for 22 hours the reaction mixture was poured into 100 mL of saturated NaHCO3 solution containing 100 mL of crushed ice, basified with additional solid NaHCO3 powder until the rose color dissipated and extracted twice with ether. The combined organic extracts were washed with saturated NaHCO3 (1×75 mL), saturated brine (1×100 mL), dried with anhydrous NaSO4 and concentrated in vacuo. Flash chromatography with 100 g of silica gel using ethyl acetate-hexane (1:2) afforded 4.07 g of the title compound as a golden oil.

المصدر