Reaction #63525

Reaction equation

ethyl acetate

N-methylcyclohexylamine

4-chlorobutyryl chloride

triethylamine

→

N-methyl-N-cyclohexyl-4-chlorobutyramide

Solvents

water

Conditions

Workup

1. 1
   Otherat 10° to 20° C.
2. 2
   Temperaturecooling
3. 3
   workup.ADDITIONis added to the reaction mixture
4. 4
   OtherThe organic layer is separated
5. 5
   Washwashed with water an aqueious saturated potassium carbonate solution, 10% aqueous hydrochloric acid and water in order
6. 6
   Dryingdried over anhydrous sodium sulfate
7. 7
   FiltrationAfter filtering off sodium sulfate
8. 8
   Concentrationthe mother liquor is concentrated
9. 9
   workup.DISTILLATIONdistilled under reduced pressure

Procedure

To ethyl acetate (400 ml) is added N-methylcyclohexylamine (26 ml), and to the mixture are added dropwise with stirring 4-chlorobutyryl chloride (25 ml) and triethylamine (33.5 ml) over a period of 20 minutes with keeping the inner temperature at 10° to 20° C. by ice-cooling. The mixture is further stirred at room temperature for one hour. After the reaction, water is added to the reaction mixture. The organic layer is separated and washed with water an aqueious saturated potassium carbonate solution, 10% aqueous hydrochloric acid and water in order, and then dried over anhydrous sodium sulfate. After filtering off sodium sulfate, the mother liquor is concentrated and distilled under reduced pressure to give N-methyl-N-cyclohexyl-4-chlorobutyramide (41.5 g), b.p. 133°-136° C./2 mmHg.

Source