Sodium Carbonate → HCID 86755083, compound

HRID 850210Notes

Reaction equation

HRID 850210 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:23][CH:24]=[CH:25][C:26]#[C:27][C:28]([CH3:31])([CH3:30])[CH3:29]>CN(C)C=O>[CH3:29][C:28]([CH3:31])([CH3:30])[C:27]#[C:26]/[CH:25]=[CH:24]\[CH2:23][N:2]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:1]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 193663851-([1,1'-Biphenyl]-2-yl)-N-methylmethanamineHCID 454895941-Bromo-6,6-dimethylhept-2-en-4-yne

Product 1

HCID 86755083HCID 86755083, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

N-methyl-2-phenylbenzylamine (2.57 g) was dissolved in 17 ml of N,N-dimethylformamide (DMF), followed by the addition of 1.39 g of sodium carbonate. While stirring the resulting mixture under ice cooling, a solution of 2.5 g of 1-bromo-6,6-dimethyl-2-hepten-4-yne in DMF was added dropwise. The temperature of the mixture was allowed to rise to room temperature, at which a reaction was allowed to proceed for 16 hours. After the reaction mixture was concentrated under reduced pressure, water and diethyl ether were added to subject the resulting concentrate to liquid-liquid extraction. The organic layer was collected and then dried over magnesium sulfate. The solvent was then distilled off. The residue was purified by chromatography on a silica gel (eluent:hexane/ethyl acetate=10/1), whereby trans-N-(6,6-dimethyl-2-hepten-4-yn-1-yl)-N-methyl-2-phenylbenzylamine (Compound 5) and cis-N-(6,6-dimethyl-2-hepten-4-yn-1-yl)-N-methyl-2-phenylbenzylamine (Compound 6) were obtained in amounts of 2.15 g (yield: 54.5%) and 0.73 g (yield: 18.5%), respectively. The followings are their NMR spectrum data:

Workup

  1. customto rise to room temperature, at which
  2. concentrationAfter the reaction mixture was concentrated under reduced pressure, water and diethyl ether
  3. additionwere added
  4. concentrationconcentrate to liquid-liquid extraction
  5. customThe organic layer was collected
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was then distilled off
  8. customThe residue was purified by chromatography on a silica gel (eluent:hexane/ethyl acetate=10/1), whereby trans-N-(6,6-dimethyl-2-hepten-4-yn-1-yl)-N-methyl-2-phenylbenzylamine (Compound 5)

Sources & evidence

ORD record
ord-9b699f463dfa4f5aac376da2c8f7c895
Source dataset
uspto-grants-2000_01
Patent number
US06015925

Reaction notes

Loading…