Methanol → N-Methyl-N-naphthylmethylamine

HRID 2269226Notes

Reaction equation

HRID 2269226 reaction equation
[CH3:1][NH2:2].CO.CO.Cl[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1>C(N(CC)CC)C>[CH3:1][NH:2][CH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 68451-ChloromethylnaphthaleneHCID 57454252Monomethylamine methanol

Product 1

HCID 84474N-Methyl-N-naphthylmethylamineYield 91.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

1.14 g (11.3 mmol), of triethylamine was mixed with a 40% methylamine-methanol solution and 5 ml of the methanol containing 2.00 g (11.3 mmol), of 1-chloromethylnaphthalene was dropped while stirring in an ice bath. After dropping, the reaction mixture was taken out of the ice bath and stirred at room temperature for 60 hours. The solvent was distilled off under reduced pressure and extracted with ether-2N hydrochloric acid. The organic extract was washed with saturated saline and dried with sodium sulfate. Then, the solvent was distilled off under reduced pressure to obtain 1.78 g (yield: 91.9%), of the target compound as a pale yellow oil.

Workup

  1. additionwas dropped
  2. stirringstirred at room temperature for 60 hours
  3. distillationThe solvent was distilled off under reduced pressure
  4. extractionextracted with ether-2N hydrochloric acid
  5. extractionThe organic extract
  6. washwas washed with saturated saline
  7. dry with materialdried with sodium sulfate
  8. distillationThen, the solvent was distilled off under reduced pressure
  9. customto obtain 1.78 g (yield: 91.9%)

Sources & evidence

ORD record
ord-f1c24f46eb7c451983b57be8c374687a
Source dataset
uspto-grants-2001_12
Patent number
US06329399B1

Reaction notes

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