Reaction #1483047

Reaction equation

N,N-dibutylamine

Valeroyl chloride

dibutylamine

→

N,N-dibutylpentanamide

Solvents

diethyl ether

diethyl ether

Conditions

Workup

1. 1
   workup.ADDITIONa round-bottom flask containing a magnetic stirring bar
2. 2
   OtherThe flask was removed from ice
3. 3
   ExtractionTwo 500 mL extractions
4. 4
   Otherto remove the excess amine and ammonium chloride byproduct
5. 5
   Dryingdried with MgSO4
6. 6
   OtherDiethyl ether was removed under rotary evaporation and high vacuum

Procedure

a round-bottom flask containing a magnetic stirring bar, diethyl ether (400 mL) and N,N-dibutylamine (37 mL, 0.22 mol, 2.2 equiv.) was cooled in ice for 30 minutes. Valeroyl chloride (12.0 mL, 0.099 mol, 1.0 equiv.) was combined with diethyl ether (75 mL) and added dropwise over 30 minutes to the stirring dibutylamine solution on ice. A white precipitate, likely the amine's chloride salt, was observed. The flask was removed from ice and stirred at room temperature for 3 h. Two 500 mL extractions were performed with dilute HCl (10 mL conc. HCl per 500 mL extraction) to remove the excess amine and ammonium chloride byproduct. The diethyl ether layer was retained and dried with MgSO4. Diethyl ether was removed under rotary evaporation and high vacuum, leaving crude N,N-dibutylpentanamide.

Source