Reaction #684956

Reaction equation

Dimethylamine

triethylamine

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide

4-pentynoic acid

→

title compound

N,N-dimethyl-4-pentynamide

Solvents

methylene chloride

Conditions

Workup

1. 1
   WashThe reaction mixture was washed successively with 1 N hydrochloric acid
2. 2
   Dryinga saturated aqueous sodium hydrogencarbonate solution, water, and saturated brine, dried over anhydrous magnesium sulfate
3. 3
   Concentrationconcentrated under reduced pressure

Procedure

Dimethylamine (2 M solution in tetrahydrofuran, 8.53 ml), triethylamine (2.59 ml), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (3221 mg), were added to a solution of 4-pentynoic acid (552 mg) in methylene chloride (150 ml) and this reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was washed successively with 1 N hydrochloric acid, a saturated aqueous sodium hydrogencarbonate solution, water, and saturated brine, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure to give the title compound (129 mg). The obtained compound was used in the following reaction without further purification.

Source