Dimethylformamide → trans-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-(3-bromo-4-fluorobenzyl)amine

HRID 1356805Notes

Reaction equation

HRID 1356805 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[CH2:5]CN.C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:19][CH:20]=[CH:21][C:22]#[C:23][C:24]([CH3:27])([CH3:26])[CH3:25].[CH3:28][N:29](C)C=O>>[CH3:25][C:24]([CH3:27])([CH3:26])[C:23]#[C:22]/[CH:21]=[CH:20]/[CH2:19][N:29]([CH2:5][C:4]1[CH:8]=[CH:9][C:10]([F:11])=[C:2]([Br:1])[CH:3]=1)[CH3:28]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 10340Sodium CarbonateHCID 185094572-(3-Bromo-4-fluorophenyl)ethan-1-amineHCID 454895941-Bromo-6,6-dimethylhept-2-en-4-yne

Product 1

HCID 18509463trans-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-(3-bromo-4-fluorobenzyl)amineYield 42.9%

Procedure

N-(3-bromo-4-fluorobenzyl)methylamine (4.00 g; 18.3 mmol) and sodium carbonate (2.78 g; 26.3 mmol) were added to N,N-dimethylformamide (35 ml). While the mixture was stirred at room temperature, 1-bromo-6,6-dimethyl-2-hepten-4-yne (3.51 g; 17.5 mmol) in N,N-dimethylformamide (15 ml) was added dropwise. The mixture was stirred for 4 hours at room temperature, and the mixture was poured into ice+saturated aqueous sodium bicarbonate solution, followed by extraction with ethyl acetate (100 ml). The organic layer was washed with saturated aqueous sodium bicarbonate solution and then with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1), to thereby yield 2.54 g of the target compound as orange oily matter (yield: 42.9%).

Workup

  1. stirringThe mixture was stirred for 4 hours at room temperature
  2. additionthe mixture was poured into ice+saturated aqueous sodium bicarbonate solution
  3. extractionfollowed by extraction with ethyl acetate (100 ml)
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
  5. dry with materialwith saturated brine, and dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-a7929d46d94345ffb6dfd0e90b70a8dc
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

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