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ChemicalBook CAS DataBase List Diphenhydramine
58-73-1

Diphenhydramine synthesis

13synthesis methods
Diphenhydramine, 2-diphenylmethoxy-N,N-dimethylamine (10.2.5), is synthesized by the esterification of 2-dimethylaminoethanol with benzhydrylbromide [35–37].

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Yield:58-73-1 98%

Reaction Conditions:

with di(n-butyl)tin oxide;3-methyl-1-propylimidazolium bromide in neat (no solvent) for 8 h;Reflux;Reagent/catalyst;

Steps:

1-6 Example 5
36.8 g (0.2 mol) of diphenylmethanol and dimethylaminoethanol 53.4 g (0.6 mol) were added to a 250 mL single-mouth bottle. 2.6 g (7% of the mass of diphenylmethanol) of dibutyltin oxide andIonic liquid 1-methyl-3-n-propylimidazolium bromide 1.8 g (5% by mass of diphenylmethanol), the reaction mixture was reacted under stirring at reflux. The reaction was examined by gas chromatography to determine the extent of the reaction. After the reaction for 8 hours, the reaction was completed, and the excess dimethylaminoethanol (which can be recovered and reused) was distilled off under reduced pressure, and then the temperature was elevated to obtain 50.0 g of diphenhydramine, and the yield was 98.0%. The purity is 99.5%.

References:

Jiaxing College;Zong Qianshou;Wang Jianbo;Song Xixi;Qiu Guanyinsheng;Bao Lin;Miao Chengping;Zhang Yang CN104892435, 2016, B Location in patent:Paragraph 0023-0034

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