ChemicalBook CAS DataBase List 1,3-Adamantanediamine

1,3-Adamantanediamine synthesis

5synthesis methods

Product Name:1,3-Adamantanediamine
CAS Number:10303-95-4
Molecular formula:C10H18N2
Molecular Weight:166.26

1,3-Adamantanediamine synthesis: 1,3-Adamantane dicarboxylic acid (12 g) was mixed with 50 mL of SOCl2 and the mixture was refluxed for 3 h. Excessive SOCl2 was evaporated and 1,3-adamantane dicarbonyl dichloride was obtained as white solid, dissolved in dried benzene and added to cold ammonia solution slowly, during which a white precipitate was formed gradually filtered and then washed the precipitate several times with water to give 1,3-disaminoacyladamantane as white solid, recrystallized from ethanol. White solid, yield 10.58 g (89 %).

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Yield:-

Steps:

Multi-step reaction with 3 steps
1: bromine; iron / 1,1,2-trichloro-1,2,2-trifluoro-ethane / 3 h / 20 °C
2: 74 percent / azidotrimethylsilane; SnCl₄ / CH₂Cl₂ / 12 h / Heating
3: hydrogen / Pd on carbon / tetrahydrofuran / 22 h / 20 °C / 2068.59 Torr

References:

Davis, Matthew;Nissan, David [Synthetic Communications,2006,vol. 36,# 15,p. 2113 - 2119]