Acetate → N-3-methoxypropyl-N-ethylguanidine

HRID 635550

Reaction equation

[CH2:1]([NH:3][CH2:4][CH2:5][CH2:6][O:7][CH3:8])[CH3:2].C(O)(=O)C.[N:13]#[C:14][NH2:15].C([O-])(=O)C>>[CH3:8][O:7][CH2:6][CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[C:14]([NH2:15])=[NH:13]

Participants

Reactant 4

HCID 175Acetate

HCID 176Acetic Acid

HCID 9864Cyanamide

HCID 12238051N-ethyl-3-methoxypropan-1-amine

Product 1

HCID 21259568N-3-methoxypropyl-N-ethylguanidineYield 50%

Conditions

Temperature: 90 °C

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.

Workup

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

Sources & evidence

ORD record: ord-ff708f5c603d451890977befbe37c97d
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06187955B1

Linked notes

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