ChemicalBook CAS DataBase List Histamine dihydrochloride

Histamine dihydrochloride synthesis

5synthesis methods

Product Name:Histamine dihydrochloride
CAS Number:56-92-8
Molecular formula:C5H11Cl2N3
Molecular Weight:184.07

A synthesis method of histamine dihydrochloride: add 15g L-histidine, 1.5g cuprous bromide, 4ml p-methylacetophenone and 120ml in a 200ml flask equipped with mechanical stirring and a thermometer Methylcyclohexanol, evacuated and filled with nitrogen to protect from light. Heating to 100-110°C for 10 hours. Cool the temperature to <30°C, feed hydrogen chloride gas, use an ice bath to control the temperature <30°C, and feed the gas for 2 to 3 hours. The solution was filtered and washed with dichloromethane, and the filter cake was dried in vacuo for 4 hours to give an off-white solid. The solid was dissolved in 85% methanol solution, hydrogen chloride gas was introduced twice under stirring in an ice bath <30°C. After the reaction, Egret Z activated carbon was added to decolorize, and the filtrate was cooled and crystallized after filtration. The solid was suction filtered and then dried in vacuo to obtain 4.11 g of a white solid with a yield of 23%.

71-00-1 Synthesis

71-00-1
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$7.00/5g

56-92-8
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$5.00/50mg

Yield:56-92-8 92%

Reaction Conditions:

Stage #1:L-histidine with (R)-Carvone in propan-1-ol at 190; under 11251.1 Torr; for 0.2 h;Sealed tube;
Stage #2: with hydrogenchloride in propan-1-ol;water at 190; for 0.0833333 h;

Steps:

General “One-Pot” Procedure for the Decarboxylation of Amino Acids
General procedure: General “One-Pot” Procedure for the Decarboxylation of Amino Acids [0045] A magnetic stir bar, 3 mL of n-PrOH, 10 mmol of R-Carvone, and 5 mmol of amino acid were charged to a pressure vessel. The vessel was heated from room temperature to 190° C. over 5 min with stirring. If necessary the reaction vessel was maintained at 190° C. for additional time until the slurry became clear. The vessel was allowed to cool to below the solvent boiling point, carefully vented to release evolved CO₂, and 10 mL of 2M HCl was added. The vessel was heated to 190° C. over 5 min with stirring and allowed to cool. The aqueous reaction mixture was washed three times with 25 mL of ether and water solvent distilled off from the hydrochloride salt. The hydrochloride salt was transferred to a vacuum oven and dried overnight at 150° C. and 10 Torr. The hydrochloride salt was then weighed and analyzed via IR and NMR.; histamine dihydrochloride, δ_H3.00 2H t J=8, 3.18 2H t J=8, 7.23 1H s, 8.50 1H s; δ_C22.26, 38.11, 117.08, 128.49, 134.00

References:

Morrison, Richard W.;Jackson, Douglas Michael US2014/275569, 2014, A1 Location in patent:Page/Page column 0045; 0052; 0066; 0067

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