Reaction #502093

Reaction equation

1-hydroxybenzotriazole

1-benzyl-N,N-dimethylcyclohexane-1,4-diamine

4-[2-(2-fluorophenyl)ethylcarbamoyl]butyric acid

N,N-diisopropylcarbodiimide

→

glutaric acid (4-benzyl-4-dimethylaminocyclohexyl)amide

Solvents

diethyl ether

DMF

Conditions

Workup

1. 1
   Otherthe crude product (1.65 g yellow solid) similarly isolated

Procedure

As described for Example 341, 0.95 mg 4-[2-(2-fluorophenyl)ethylcarbamoyl]butyric acid and 0.87 1-benzyl-N,N-dimethylcyclohexane-1,4-diamine were converted in 5 ml DMF in the presence of 0.59 ml N,N-diisopropylcarbodiimide and 0.50 g 1-hydroxybenzotriazole and the crude product (1.65 g yellow solid) similarly isolated. 720 mg of the non-polar diastereoisomer of glutaric acid (4-benzyl-4-dimethylaminocyclohexyl)amide was obtained by column chromatography on silica gel (3.0×20 cm) with 450 ml diethyl ether, followed by 450 ml diethyl ether/methanol (V:V=4:1) and 450 ml diethyl ether/methanol (V:V=1:1), was dissolved in 25 ml 2-butanone, 25 ml ethyl acetate and converted into the corresponding hydrochloride by adding 28 μl water and 198 μl chlorotrimethylsilane (657 mg of vitreous solid).

Source