Reaction #93169

Reaction equation

1-[2-(4-pyridinylamino)benzoyl]piperidine

sodium amide

ethyl iodide

→

1-{2-[ethyl-(4-pyridinyl)amino]benzoyl}piperidine

Yield 100.8%

Solvents

dimethylformamide

dimethylformamide

Conditions

Workup

1. 1
   workup.STIRRINGThe reaction mixture was stirred for two hours
2. 2
   Filtrationfiltered
3. 3
   Concentrationconcentrated in vacuo
4. 4
   OtherThe residue was partitioned between water and ether
5. 5
   Otherthe ether-soluble material recovered (15.2 g)
6. 6
   OtherThe latter was recrystallized from ethyl acetate

Procedure

A solution of 22.4 g of 1-[2-(4-pyridinylamino)benzoyl]piperidine (Example 1b) in 45 ml of dimethylformamide was added dropwise to a suspension of sodium amide (from 4.8 g of 50% oil suspension, washed free of oil) in 115 ml of dimethylformamide. The mixture was stirred for one hour, and then 6.5 g of ethyl iodide was added dropwise. The reaction mixture was stirred for two hours, then filtered and concentrated in vacuo. The residue was partitioned between water and ether and the ether-soluble material recovered (15.2 g). The latter was recrystallized from ethyl acetate--pentane to give 13 g of 1-{2-[ethyl-(4-pyridinyl)amino]benzoyl}piperidine, m.p. 123°-124° C.

Source