Iodoethane → 1-Ethyl-2,2,4-trimethyl decahydroquinoline

HRID 616234Notes

Reaction equation

HRID 616234 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

Reactant 3

HCID 6340IodoethaneHCID 92911DecahydroquinolineHCID 226287862,2,4-Trimethyldecahydroquinoline

Product 1

HCID 205431051-Ethyl-2,2,4-trimethyl decahydroquinoline

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.

Workup

  1. customwas placed into a reactor vessel
  2. customequipped
  3. temperaturefor heating
  4. customA thick slurry formed which
  5. filtrationwas filtered out
  6. washwashed wih acetone
  7. washThe acetone wash liquid
  8. concentrationwas then concentrated
  9. distillationdistilled

Sources & evidence

ORD record
ord-a145fdc146fe40ff84499982d8629ad7
Source dataset
uspto-grants-1978_02
Patent number
US04073770

Reaction notes

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