Diethyl Ether → 1-(Bicyclo[2.2.1]hept-5-en-2-yl)methanamine

HRID 1622072Notes

Reaction equation

HRID 1622072 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC.[CH:12]12[CH2:18][CH:15]([CH:16]=[CH:17]1)[CH2:14][CH:13]2[C:19]#[N:20].[H][H].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>O>[CH:12]12[CH2:18][CH:15]([CH:16]=[CH:17]1)[CH2:14][CH:13]2[CH2:19][NH2:20]

Participants

7

Reactant 5

HCID 3283Diethyl Ether2×HCID 7218Bicyclo[2.2.1]heptane-2-carbonitrileHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 2471821-(Bicyclo[2.2.1]hept-5-en-2-yl)methanamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A three-neck flask is equipped with mechanical stirrer, reflux condenser and dropping funnel. The flask is charged under N2, with 42 ml of a 1.0 M solution of lithium aluminum hydride in anhydrous ether (42 mmol). A solution of 5 g of 5-Norbornene-2-carbonitrile (bicyclo[2.2.1]hept-5-ene-2-carbonitrile) in 45 ml of ether (42 mmol, 1.0 M) is added dropwise through the addition funnel at a rate that allows a gentle reflux. After one hour, the mixture is cooled to 0° C. and water is added dropwise until hydrogen gas liberation is no longer observed. To this, 100 ml of 20% sodium potassium tartrate is added and produces a clear solution. The reaction solution is transferred to a separatory funnel, and the aqueous phase is collected and washed with 3×50 ml portions of ether. The combined ether fractions are dried with calcium sulfate and solvent is removed by rotary evaporation yielding a yellow oil. This product is further distilled under reduced pressure to yield a clear oil.

Workup

  1. customA three-neck flask is equipped with mechanical stirrer
  2. temperaturereflux condenser
  3. customproduces a clear solution
  4. customThe reaction solution is transferred to a separatory funnel
  5. customthe aqueous phase is collected
  6. washwashed with 3×50 ml portions of ether
  7. dry with materialThe combined ether fractions are dried with calcium sulfate and solvent
  8. customis removed by rotary evaporation
  9. customyielding a yellow oil
  10. distillationThis product is further distilled under reduced pressure
  11. customto yield a clear oil

Sources & evidence

ORD record
ord-99d3bd18a3144b7d8502875909a7212b
Source dataset
uspto-grants-2014_07
Patent number
US08778846B2

Reaction notes

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