[C:1]1(=[N:13][OH:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:17][N:18]([CH3:23])[CH2:19][CH2:20][CH2:21]Cl.Cl.[OH-].[NH4+]>C1(C)C=CC=CC=1>[CH3:17][N:18]([CH2:19][CH2:20][CH2:21][O:14][N:13]=[C:1]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH3:23]A solution of 19.73 g. (0.1 moles) of cyclododecanone oxime in 200 ml. of anhydrous toluene is dropwise added at 85° C. under continuous stirring to a suspension of 2.4 g. (0.1 moles) of sodium hydride in 50 ml. of anhydrous toluene, and the mixture is refluxed for 2 hours. Then 13.3 g. (0.11 moles) of 1-dimethylamino-3-chloropropane is added to the reaction mixture. After refluxing for 10 hours the mixture is cooled to room temperature, washed with 100 ml of water and extracted with a 10% solution of hydrochloric acid containing 0.11 moles of hydrochloric acid. Then the solution cooled to 0° C. is made alkaline to pH 10 with an aqueous solution of ammonium hydroxide. The base separated as an oil is extracted with dichloromethane and the solvent is removed. Yield: 21.2 g. (75.07%). Hydrogen fumarate, m.p.: 116°-118° C.
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