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

HRID 2285996Notes

Reaction equation

HRID 2285996 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-ee40aa3c972e40efbede54eecd5d9093
Source dataset
uspto-grants-1982_04
Patent number
US04326061

Reaction notes

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