Water → 40137-00-6

HRID 1019343Notes

Reaction equation

HRID 1019343 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[CH2:6]=[CH:7][C:8](=[CH2:10])[CH3:9].[CH2:11]([Li])[CH2:12][CH2:13]C.O.[CH3:17][CH2:18]CCCC>>[CH2:1]([N:3]([CH2:17][CH3:18])[CH2:4][CH3:5])/[CH:2]=[C:12](\[CH2:11][CH2:6][CH:7]=[C:8]([CH3:9])[CH3:10])/[CH3:13]

Participants

6

Reactant 5

HCID 962WaterHCID 6557IsopreneHCID 8021DiethylamineHCID 8058HexaneHCID 178418339Butyllithium

Product 1

HCID 624334340137-00-6

Procedure

A solution prepared by mixing 2.93 g (40.0 mmol) of diethylamine with 18.0 ml (180 mmol) of isoprene was introduced into a 100-ml pressure tube in a nitrogen atmosphere- Thereto was gradually added dropwise at 0° C. a solution (1.6 M solution) prepared by dissolving 0.064 g of n-butyllithium (1.0 mmol) in 0.63 ml of hexane. This mixture was stirred first at room temperature for 15 minutes and then at 90° C. for 2.5 hours. To the resultant reaction mixture was added 0.3 ml of water to deactivate the catalyst. After liquid separation, the organic layer was separated and distilled to recover the unreacted isoprene. Subsequently, the concentrate remaining after the isoprene recovery was distilled under reduced pressure to obtain 7.29 g (34.8 mmol; GC yield, 87.0%) of the target mixture comprising α-neryldiethylamine and neryldiethylamine.

Workup

  1. customA solution prepared
  2. additionwas introduced into a 100-ml pressure tube in a nitrogen
  3. customprepared
  4. waitat 90° C. for 2.5 hours
  5. customTo the resultant reaction mixture
  6. customAfter liquid separation
  7. customthe organic layer was separated
  8. distillationdistilled
  9. customto recover the unreacted isoprene
  10. distillationwas distilled under reduced pressure
  11. customto obtain

Sources & evidence

ORD record
ord-5d2298ca184043678c54d35a7b719a18
Source dataset
uspto-grants-2002_11
Patent number
US06486353B2

Reaction notes

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