Dimethylamine → N,N,3,7-tetramethylocta-2,6-dien-1-amine

HRID 1031410Notes

Reaction equation

HRID 1031410 reaction equation
[CH2:1](Br)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4].[CH3:12][NH:13][CH3:14]>C(O)C>[CH3:12][N:13]([CH3:14])[CH2:1][CH:2]=[C:3]([CH3:4])[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 53658672,6-Octadiene, 1-bromo-3,7-dimethyl-, (2E)-

Product 1

HCID 324494N,N,3,7-tetramethylocta-2,6-dien-1-amineYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Geranylbromide (20 g) in ethanol (50 ml) was added to 33% dimethylamine in industrial methylated spirits (240 ml) and the mixture was heated at reflux for 8 hours. The reaction mixture was evaporated to dryness, mixed with 2N sodium hydroxide (50 ml) and then extracted with diethyl ether (2×100ml). The ether extracts were combined and washed with water (50 ml), then dried with anhydrous magnesium sulphate and evaporated to dryness. The resulting orange oil was purified by chromatography (with a gradient CH2Cl2 :MeOH system as eluent) to give 1-dimethylamino-3.7-dimethyl-2,6-octadiene as an oil (12.1 g, 72%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 8 hours
  3. customThe reaction mixture was evaporated to dryness
  4. additionmixed with 2N sodium hydroxide (50 ml)
  5. extractionextracted with diethyl ether (2×100ml)
  6. washwashed with water (50 ml)
  7. dry with materialdried with anhydrous magnesium sulphate
  8. customevaporated to dryness
  9. customThe resulting orange oil was purified by chromatography (with a gradient CH2Cl2

Sources & evidence

ORD record
ord-ca449181923b4f8b8c11ce451cce48b7
Source dataset
uspto-grants-1990_09
Patent number
US04954339

Reaction notes

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