Reaction #859

Reaction equation

N-ethyl-3-methoxypropylamine

acetic acid

acetate

cyanamide

→

title compound

Yield 50.0%

N-3-methoxypropyl-N-ethylguanidine

Yield 50.0%

Solvents

Conditions

Workup

1. 1
   OtherAfter 12 hours of the reaction
2. 2
   Otherthe product was purified by a silica gel column chromatography (eluent, chloroform/ethanol=1/2 containing 0.5% acetic acid)

Procedure

3.00 g (25.6 mmol) of N-ethyl-3-methoxypropylamine and 1.54 g (25.6 mmol) of acetic acid were placed in a 50 ml two neck flask. While heating the flask in a 90° C. oil bath, 1.08 g (25.6 mmol) of cyanamide was added. After 12 hours of the reaction, the product was purified by a silica gel column chromatography (eluent, chloroform/ethanol=1/2 containing 0.5% acetic acid) to obtain 2.80 g of the title compound (wax-like, 12.8 mmol, 50.0% in yield) in the form of acetate. Results of the analysis of this compound are as follows.

Source