Reaction #84052

Reaction equation

6-bromo-1-benzothiophene-2-amine

pentafluorophenyl (1-azabicyclo[2.2.2]oct-3-yl)acetate hydrochloride

hydrochloric acid

carbonate

→

title compound

2-(1-Azabicyclo[2.2.2]oct-3-yl)-N-(6-bromo-1-benzothien-2-yl)acetamide hydrochloride

Solvents

DMF

acetonitrile

Conditions

Workup

1. 1
   workup.WAITAfter 3 h
2. 2
   Filtrationthe polystyrene resin is filtered off
3. 3
   Washwashed with THF
4. 4
   ConcentrationThe combined filtrates are concentrated in vacuo
5. 5
   Otherthe crude product is purified by preparative HPLC
6. 6
   OtherThe hydrochloride is prepared
7. 7
   workup.ADDITIONby mixing the product
8. 8
   Concentrationagain concentrating
9. 9
   OtherDrying under high vacuum

Procedure

89.2 mg (0.24 mmol) of pentafluorophenyl (1-azabicyclo[2.2.2]oct-3-yl)acetate hydrochloride are dissolved in 1 ml of DMF, mixed with 71.2 mg (0.31 mmol) of 6-bromo-1-benzothiophene-2-amine and stirred at room temperature overnight. 1 g of MP-carbonate (polymer-bound carbonate, capacity: 2.5-3.5 mmol/g; from Argonaut Technologies, USA) is added. After 3 h, the polystyrene resin is filtered off and washed with THF. The combined filtrates are concentrated in vacuo, and the crude product is purified by preparative HPLC. The hydrochloride is prepared by mixing the product with a mixture of 1 M hydrochloric acid and acetonitrile and again concentrating. Drying under high vacuum results in 14 mg (14% of theory) of the title compound.

Source