[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[C:9]12([CH2:19][CH2:20][N:21]3[CH:25]=[CH:24][N:23]=[CH:22]3)[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH2:10]1)[CH2:16]2>C(O)C>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[C:9]12([CH2:19][CH2:20][N:21]3[CH:25]=[CH:24][N:23]=[CH:22]3)[CH2:10][CH:11]3[CH2:17][CH:15]([CH2:14][CH:13]([CH2:12]3)[CH2:18]1)[CH2:16]2A solution of fumaric acid (0.5 g, 4.31 mmol) in boiling ethanol (15 ml) was added to a solution of 1-[2-(1-Adamantyl)ethyl]imidazole (1.0 g, 4.34 mmol) in hot ethanol (10 ml). After boiling for 0.15 h, the mixture was concentrated to afford a white solid. Recrystallisation of the solid from ethyl acetate gave 1-[2-(1-adamantyl)ethyl]imidazole hydrogen fumarate as a colourless solid, m.p. 117°-118°.
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