Uses
1-Bromo-3,5-dimethyladamantane (cas# 941-37-7) is a compound useful in organic synthesis.
Description
1-Bromo-3,5-dimethyladamantane is a precursor substance of memantine and memantine hydrochloride (MH), which can be synthesised by direct amination with thiourea. MH is an FDA-approved first-line treatment for moderate to severe Alzheimer's disease.
Chemical Properties
Clear Colorless Oil
Uses
1-Bromo-3,5-dimethyladamantane was used in the one pot synthesis of 1,3-dicarbonyl adamantanes. It was also used in the synthesis of 3,5-dimethyladamantan-1-ol.
Synthesis
A) Add 59.9 g (0.345 mol) of bromine, 10 g (0.075 mol) of anhydrous aluminum trichloride, and 37.8 g of 1,2-dichloroethane to the reactor with thorough stirring; B) Heat the reaction mixture A to 15°C; C) Add 50 g (0.3 mol) of 1,3-dimethyladamantane to the mixture obtained in step B, and absorb the resulting gas using a 5% sodium hydroxide solution; D) Add 400 g of saturated sodium bisulfite solution to reaction mixture B until the red color of the reaction solution completely disappears, and separate the organic phase C and the aqueous phase D; and D) Add 400 g of saturated sodium bisulfite solution to the reaction mixture B until the red color of the reaction solution completely disappears, and separate the organic phase C and the aqueous phase D; E) Wash the organic phase C with 400 g of water, and then dry it with 20 g of anhydrous sodium sulfate; F) Perform distillation on the organic phase C obtained in step E to obtain the crude product E; G) Perform decompression distillation on the crude product E to obtain the 1-(3-methyladamantyl)-1,3-dimethyladamantane. G) the crude product E was distilled under reduced pressure to obtain 1-bromo-3,5-dimethyladamantane in 92% yield and ≥99% purity by gas chromatography.
References
[1] Patent: CN104592034, 2016, B. Location in patent: Paragraph 0092-0099
[2] Asian Journal of Chemistry, 2012, vol. 24, # 11, p. 5107 - 5110
[3] Russian Journal of Organic Chemistry, 2015, vol. 51, # 2, p. 184 - 187
[4] Zh. Org. Khim., 2015, vol. 51, # 2, p. 196 - 199
[5] Patent: US5061703, 1991, A
