ChemicalBook CAS DataBase List Ethoxyamine hydrochloride

Ethoxyamine hydrochloride synthesis

5synthesis methods

Product Name:Ethoxyamine hydrochloride
CAS Number:3332-29-4
Molecular formula:C2H8ClNO
Molecular Weight:97.54

1914-21-2
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3332-29-4
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Yield:3332-29-4 100%

Reaction Conditions:

Stage #1: N-ethoxyphthalimidewith methylhydrazine in dichloromethane at 0 - 20; for 2 h;
Stage #2: with hydrogenchloride in 1,4-dioxane at 0;

Steps:

1-5 Preparation of SAC-1013

After 500 mg of hydroxyphthalimide (Aldrich) was dissolved in 5 ml of dimethylformamide under argon flow, 0.27 ml of iodinated ethane (Aldrich) was added, and 0.5 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene (Aldrich) was slowly added. After the mixture was stirred at 60° C. for 2 hours, the temperature was again lowered to room temperature, and then the reaction was stopped by adding a 2 N hydrochloric acid solution. The reaction liquid was diluted by adding 20 ml of ethyl acetate, followed by drying over magnesium sulfate and then filtration. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography using a mixture eluent of ethyl acetate/hexane (1:5) and then dried to obtain 518 mg of a compound (yield: 88%). The compound was dissolved in 5 ml of dichloromethane, and 0.11 ml of methyl hydrazine (TCI) was slowly added at 0° C. After the reaction liquid was stirred at room temperature for 2 hours, the temperature was again lowered to 0° C. The generated solid was then filtered out, and 1 ml of a 4 M-hydrochloric acid dioxane solution (Aldrich) was added to the residual filtrate, followed by filtration and drying, to obtain 263 mg of a solid (yield: 100%). 10 mg of the obtained solid and 44 mg of SAC-0906 obtained as obtained above were dissolved in 1 ml of pyridine (Aldrich) under argon flow, followed by stirring at 80° C. for 4 hours. After the temperature was lowered to room temperature, the reaction liquid was acidified by adding a 2 N hydrochloric acid solution, followed by extraction with 20 ml of diethyl ether, drying over magnesium sulfate, and filtration. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography using a mixed eluent of ethyl acetate/hexane (1:5) to obtain the target compound SAC-1013 (46 mg, yield: 96%). ¹H-NMR (300 MHz, CDCl₃) δ5.91-5.76 (m, 2H), 5.34-5.32 (m, 1H), 5.28-5.25 (m, 1H), 5.14 (m, 1H), 4.24-4.10 (m, 3H), 4.04 (q, J=20.9 Hz, 2H), 3.64-3.48 (m, 1H), 2.42-0.60 (m, 38H)

References:

US2014/378399,2014,A1 Location in patent:Paragraph 0097