Triethylamine → N-methyl-N-(4'-isopropylbenzyl)-1-naphthylmethylamine

HRID 620895

Reaction equation

HRID 620895 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.[CH:21]([C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Cl)=[CH:26][CH:25]=1)([CH3:23])[CH3:22]>O1CCCC1>[CH3:1][N:2]([CH2:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)[CH2:28][C:27]1[CH:30]=[CH:31][C:24]([CH:21]([CH3:23])[CH3:22])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 749164-Isopropylbenzyl chlorideHCID 84474N-Methyl-N-naphthylmethylamine

Product 1

HCID 13671214N-methyl-N-(4'-isopropylbenzyl)-1-naphthylmethylamineYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.71 g (0.01 mole) of N-methyl-1-naphthylmethylamine was dissolved in 30 ml of tetrahydrofuran, and 1.2 g (0.012 mole) of triethylamine was added. With stirring at room temperature, 1.85 g (0.011 mole) of p-isopropylbenzyl chloride was added, and the mixture was reacted at room temperature for 6 hours. The reaction mixture was filtered, and the solvent was removed under reduced pressure. The residue was distributed between ether and a saturated aqueous solution of sodium hydrogen carbonate, and the organic layer was collected. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was chromatographed on a silica gel column and eluted with 4% ethyl acetate/n-hexane. The eluate was concentrated to give 2.82 g (yield 93%) of an oily substance.

Workup

  1. customthe mixture was reacted at room temperature for 6 hours
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent was removed under reduced pressure
  4. customa saturated aqueous solution of sodium hydrogen carbonate, and the organic layer was collected
  5. washThe organic layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was chromatographed on a silica gel column
  9. washeluted with 4% ethyl acetate/n-hexane
  10. concentrationThe eluate was concentrated
  11. customto give 2.82 g (yield 93%) of an oily substance

Sources & evidence

ORD record
ord-f0cb3401965b4b0a9c91437b251e1b78
Source dataset
uspto-grants-1989_04
Patent number
US04822822

Linked notes

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