Tetrahydrofuran → 2-(4-Methylbicyclo[2.2.2]oct-1-yl)ethylamine

HRID 461993Notes

Reaction equation

HRID 461993 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[CH3:12][C:13]12[CH2:20][CH2:19][C:16]([CH2:21][C:22]#[N:23])([CH2:17][CH2:18]1)[CH2:15][CH2:14]2>O>[CH3:12][C:13]12[CH2:20][CH2:19][C:16]([CH2:21][CH2:22][NH2:23])([CH2:17][CH2:18]1)[CH2:15][CH2:14]2

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 21392721HCID 21392721, compound

Product 1

HCID 213919902-(4-Methylbicyclo[2.2.2]oct-1-yl)ethylamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.043 Mole of lithium aluminum hydride is dissolved in 100 ml. of anhydrous tetrahydrofuran, under nitrogen, at 0° C and then 0.043 mole of 4-methylbicyclo[2.2.2]oct-1-yl acetonitrile in 100 ml. of anhydrous tetrahydrofuran is added dropwise. The solution is allowed to warm to room temperature, then stirred for five minutes and then 5 ml. of water is added dropwise. The solution is then filtered and the filter cake is washed with ethyl ether, the washings combined with the filtrate, and the solution is then dried over potassium hydroxide pellets, and filtered. The filtrate is then distilled affording 2-(4-methylbicyclo[2.2.2]oct-1-yl)ethylamine as a residue.

Workup

  1. customat 0° C
  2. filtrationThe solution is then filtered
  3. washthe filter cake is washed with ethyl ether
  4. dry with materialthe solution is then dried over potassium hydroxide pellets
  5. filtrationfiltered
  6. distillationThe filtrate is then distilled

Sources & evidence

ORD record
ord-bea1efee6a98472a9c672162d9a0618a
Source dataset
uspto-grants-1977_12
Patent number
US04064258

Reaction notes

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