Triethylamine → N-(5,5-Dimethylhex-3-yn-1-yl)-N-methyl-1-naphthalenemethanamine

HRID 1788743Notes

Reaction equation

HRID 1788743 reaction equation
[CH3:1][C:2]([CH3:9])([CH3:8])[C:3]#[C:4][CH2:5][CH2:6]O.C(N(CC)CC)C.CS(Cl)(=O)=O.[CH3:22][NH:23][CH2:24][C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1>CN(C)C=O>[CH3:22][N:23]([CH2:24][C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1)[CH2:6][CH2:5][C:4]#[C:3][C:2]([CH3:9])([CH3:8])[CH3:1]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 84474N-Methyl-N-naphthylmethylamineHCID 103744723-Hexyn-1-ol, 5,5-dimethyl-

Product 1

HCID 128499N-(5,5-Dimethylhex-3-yn-1-yl)-N-methyl-1-naphthalenemethanamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 540 mg 5,5-dimethyl-3-hexyn-1-ol in dimethylformamide (DMF) are added, at 0° 1.2 ml triethylamine. Then are added, dropwise, with stirring, 0.335 ml methanesulfonylchloride. After 2 hours of stirring at room temperature are added 740 mg N-methyl-1-naphthylmethylamine and the mixture is heated overnight at 80°. The solvent is evaporated in vacuum, the residue distributed between saturated aqueous NaHCO3 solution and ethyl acetate, the organic phase washed, dried and evaporated. The crude residue is chromatographed over silicagel (with toluene/ethylacetate 9/1) and the title compound (Compound 1) obtained as an oil.

Workup

  1. additionThen are added
  2. stirringAfter 2 hours of stirring at room temperature
  3. temperaturethe mixture is heated overnight at 80°
  4. customThe solvent is evaporated in vacuum
  5. washthe organic phase washed
  6. customdried
  7. customevaporated
  8. customThe crude residue is chromatographed over silicagel (with toluene/ethylacetate 9/1)

Sources & evidence

ORD record
ord-c39833f6725448ef840e93d90607c1cb
Source dataset
uspto-grants-1987_08
Patent number
US04684661

Reaction notes

Loading…