Ethylene Oxide → 1-(2'-Hydroxyethyl)-2,2,4-trimethyl decahydroquinoline

HRID 616235Notes

Reaction equation

HRID 616235 reaction equation
[CH3:1][C:2]1([CH3:13])[CH2:11][CH:10]([CH3:12])[CH:9]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[NH:3]1.[CH2:14]1[O:16][CH2:15]1>C(O)C>[OH:16][CH2:15][CH2:14][N:3]1[CH:4]2[CH:9]([CH2:8][CH2:7][CH2:6][CH2:5]2)[CH:10]([CH3:12])[CH2:11][C:2]1([CH3:13])[CH3:1]

Participants

4

Reactant 2

HCID 6354Ethylene OxideHCID 226287862,2,4-Trimethyldecahydroquinoline

Product 1

HCID 205431171-(2'-Hydroxyethyl)-2,2,4-trimethyl decahydroquinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(2'-hydroxyethyl)-2,2,4-trimethyl decahydroquinoline was prepared. 150 milliliters of ethanol and 84.0 grams (0.3 mole) of 2,2,4-trimethyl decahydroquinoline of about 96% cis structure were placed in a reactor vessel equipped for heating and agitation. 15.4 grams (0.35 mole) of ethylene oxide was added dropwise to the reactor vessel and the mix then heated to reflux for 21 hours. The ethanol was then evaporated off and the reaction mixture distilled to yield 10.2 grams of a liquid product boiling at 103° - 105° C. at 0.3 mm Hg. The NMR and mass spectrometer spectra were consistent with the desired product. Calculated contents for the formula C14H27NO are 74.61% carbon, 12.08% hydrogen, and 6.22% nitrogen and the measured contents were 74.62% carbon, 12.11% hydrogen, and 6.13% nitrogen.

Workup

  1. customequipped
  2. temperaturefor heating
  3. additionthe mix
  4. temperaturethen heated
  5. temperatureto reflux for 21 hours
  6. customThe ethanol was then evaporated off
  7. distillationthe reaction mixture distilled

Sources & evidence

ORD record
ord-9bfece7e40a54ac7874674a8d600a074
Source dataset
uspto-grants-1978_02
Patent number
US04073770

Reaction notes

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