Diethylamine → 2,6-Octadien-1-amine, N,N-diethyl-3,7-dimethyl-, (2E)-

HRID 2286480Notes

Reaction equation

HRID 2286480 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].C([Li])CCC.[CH3:11][C:12]([CH3:20])=[CH:13][CH2:14][CH2:15][C:16]([CH:18]=[CH2:19])=[CH2:17].C(C(CC)/C(/C)=C/CC/C(/C)=C/CN)C.C(N)/C=C(/CCC=C(C)C)\C>CCCCCC>[CH2:1]([N:3]([CH2:19]/[CH:18]=[C:16](/[CH2:15][CH2:14][CH:13]=[C:12]([CH3:20])[CH3:11])\[CH3:17])[CH2:4][CH3:5])[CH3:2]

Participants

7

Reactant 5

HCID 8021DiethylamineHCID 31253MyrceneHCID 5475462GeranylamineHCID 87531006HCID 87531006, compoundHCID 178418339Butyllithium

Product 1

HCID 63906212,6-Octadien-1-amine, N,N-diethyl-3,7-dimethyl-, (2E)-

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
50 °C

Procedure

Dry diethylamine (84 ml, 0.816 mole) was charged into a 500 ml 3 necked flask equipped with reflux condenser, thermometer, addition funnel and magnetic stirrer. The flask was swept out with dry nitrogen and maintained under a nitrogen blanket. Butyl lithium (16.6 ml, 2.2 M) in hexane was then added and the temperature raised to 50° C. After 15 minutes 200 ml 85% myrcene (1 mole) was added. The mixture exothermed and was cooled to 60°. After 4 hours at 60°, gas chromatography indicated that the amine had been converted to virtually a single product in high yield. Distillation gave a fraction boiling at 108° C./7 mm which was identified as diethylgeranylamine. The yield was 148.7 g (87% based on the amine used) of a product which was 96% "geranyl amine". (See Table I).

Workup

  1. customequipped
  2. temperaturewith reflux condenser
  3. additionthermometer, addition funnel and magnetic stirrer
  4. temperaturemaintained under a nitrogen blanket
  5. temperaturewas cooled to 60°
  6. distillationDistillation
  7. customgave a fraction boiling at 108° C./7 mm which

Sources & evidence

ORD record
ord-c4ac54db83bd4609b077b1cdd4538bcf
Source dataset
uspto-grants-1981_05
Patent number
US04266087

Reaction notes

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