Reaction #1885019

Reaction equation

iso-propyl 4-acetoxybut-2-ynecarboxylate

1-(6-chloropyridin-3-yl)-N-methylmethanamine

→

iso-Propyl 4-acetoxy-3-[(6-chloropyrid-3-ylmethyl)amino]but-2-enecarboxylate

Solvents

THF

tetrahydrofuran

Conditions

Workup

1. 1
   Concentrationconcentrated under reduced pressure
2. 2
   Washwashed successively with dilute aqueous sulphuric acid and sodium hydrogencarbonate solution
3. 3
   DryingAfter drying over magnesium sulphate
4. 4
   Concentrationconcentrating the organic phase under reduced pressure, 120 mg (50% of theory) of iso-propyl 4-acetoxy-3-[(4-chlorobenzyl)(methyl)amino]but-2-enecarboxylate
5. 5
   Otherare obtained

Procedure

To an initial charge of 124 mg (0.672 mmol) of iso-propyl 4-acetoxybut-2-ynecarboxylate in 5 ml of anhydrous tetrahydrofuran (THF) are added dropwise 116 mg (0.739 mmol) of 1-(6-chloropyridin-3-yl)-N-methylmethanamine, dissolved in 1 ml of anhydrous THF, at room temperature. The reaction mixture is stirred at room temperature for 16 h and concentrated under reduced pressure. Subsequently, the residue is taken up with toluene and washed successively with dilute aqueous sulphuric acid and sodium hydrogencarbonate solution. After drying over magnesium sulphate and concentrating the organic phase under reduced pressure, 120 mg (50% of theory) of iso-propyl 4-acetoxy-3-[(4-chlorobenzyl)(methyl)amino]but-2-enecarboxylate are obtained.

Source