Iodoethane → 1-Ethyl-2,2,4-trimethyl decahydroquinoline
Reaction equation
N1C2C(CCCC2)C[CH2:3][CH2:2]1.[CH3:11][C:12]1([CH3:23])[CH2:21][CH:20]([CH3:22])[CH:19]2[CH:14]([CH2:15][CH2:16][CH2:17][CH2:18]2)[NH:13]1.ICC>>[CH2:2]([N:13]1[CH:14]2[CH:19]([CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:20]([CH3:22])[CH2:21][C:12]1([CH3:23])[CH3:11])[CH3:3]Participants
4
Conditions
- Temperature
- 105 °C
Procedure
1-ethyl-2,2,4-trimethyl decahydroquinoline was prepared by the reaction of the intermediate saturated decahydroquinoline with the alkyl halide. 36.3 grams (0.2 mole) of 2,2,4-trimethyl decahydroquinoline of about 76% cis structure was placed into a reactor vessel equipped for heating and agitation. 15.6 grams (0.1 mole) of iodoethane was added dropwise to the reactor vessel. The mix was heated to 105° C. while stirring for 3 hours. A thick slurry formed which was filtered out and washed wih acetone. The acetone wash liquid was then concentrated and distilled using a 3 inch Vigreaux column to yield 7.1 grams of a product boiling at 58° - 60° C. at 0.25 mm Hg. The NMR spectra of the product was consistent with the desired product, 1-ethyl-2,2,4-trimethyl decahydroquinoline. Calculated carbon, hydrogen, nitrogen content for the formula C14H27N is 80.31% carbon, 13.00% hydrogen, and 6.69% nitrogen while the measured contents were 79.93% carbon, 13.54% hydrogen, and 6.35% nitrogen respectively.