Methylamine → N,6,6-trimethylhept-2-en-4-yn-1-amine

HRID 851163Notes

Reaction equation

HRID 851163 reaction equation
Br[CH2:2][CH:3]=[CH:4][C:5]#[C:6][C:7]([CH3:10])([CH3:9])[CH3:8].[CH3:11][NH2:12]>C(O)C>[CH3:8][C:7]([CH3:10])([CH3:9])[C:6]#[C:5][CH:4]=[CH:3][CH2:2][NH:12][CH3:11]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 454895941-Bromo-6,6-dimethylhept-2-en-4-yne

Product 1

HCID 53427009N,6,6-trimethylhept-2-en-4-yn-1-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

24.3 g of 1-bromo-6,6-dimethylhept-2-en-4-yne in 750 ml of ethanol are added at -50° to 245 ml of a 33% ethanolic solution of methylamine and the mixture stirred in a closed vessel at 55° for 3 hours. The resulting mixture is concentrated in a rotary evaporator and the residue taken up with chloroform and washed with 1 N NaOH and saturated NaCl. After drying over MgSO4 the crude product is purified by chromatography on kieselgel (eluant toluene/ethylacetate; 4/1). A colourless oil is obtained (trans- and cis compound in ratio 3:1).

Workup

  1. concentrationThe resulting mixture is concentrated in a rotary evaporator
  2. washwashed with 1 N NaOH and saturated NaCl
  3. dry with materialAfter drying over MgSO4 the crude product
  4. customis purified by chromatography on kieselgel (eluant toluene/ethylacetate; 4/1)
  5. customA colourless oil is obtained (trans- and cis compound in ratio 3:1)

Sources & evidence

ORD record
ord-bc5089fc96e943809f1a810af5a4712b
Source dataset
uspto-grants-1983_05
Patent number
US04382951

Reaction notes

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