Water → Methyl[(naphthalen-2-yl)methyl]amine

HRID 1690364Notes

Reaction equation

HRID 1690364 reaction equation
[CH3:1][NH2:2].O.Br[CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1>C1COCC1>[CH3:1][NH:2][CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 703202-Bromomethylnaphthalene

Product 1

HCID 541935Methyl[(naphthalen-2-yl)methyl]amineYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 40 wt % methylamine in H2O (50 mL, 581 mmole) in THF (50 mL) at 0° C. was added 2-(bromomethyl)naphthalene (10 g, 43 mmole) in one portion. The reaction was allowed to warm to RT and stirred for 16 hr, then was then concentrated under vacuum. The residue was taken up in Et2O and washed with 1.0 N NaOH then with brine, dried (Na2SO4), and concentrated to dryness. Purification by flash chromatography on silica gel (98:2 to 9:1 CHCl3/methanol containing 5% NH4OH) gave the title compound (3.95 g, 54%) as a clear oil: 1H NMR (400 MHz, CDCl3) δ 7.85 (m, 3 H), 7.79 (s, 1 H), 7.49 (m, 3 H), 3.94 (s, 2 H), 2.53 (s, 3 H).

Workup

  1. concentrationwas then concentrated under vacuum
  2. washwashed with 1.0 N NaOH
  3. dry with materialwith brine, dried (Na2SO4)
  4. concentrationconcentrated to dryness
  5. customPurification by flash chromatography on silica gel (98:2 to 9:1 CHCl3/methanol containing 5% NH4OH)

Sources & evidence

ORD record
ord-bf71ad145d10471695f44ad52635afb5
Source dataset
uspto-grants-2012_04
Patent number
US08153652B2

Reaction notes

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