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

HRID 1362011

Reaktionsgleichung

Reaktionsgleichung von HRID 1362011
[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

Komponenten

5

Edukt 3

HCID 962WaterHCID 6329MethylamineHCID 703202-Bromomethylnaphthalene

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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, 3H), 7.79 (s, 1H), 7.49 (m, 3H), 3.94 (s, 2H), 2.53 (s, 3H).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-8812e9e3e54146059ae4da632f92fa72
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879872B2

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