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

HRID 225882

반응식

HRID 225882 반응식
[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

참가 물질

5

반응물 3

HCID 962WaterHCID 6329MethylamineHCID 703202-Bromomethylnaphthalene

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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 tide 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).

후처리

  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)

출처 및 근거

ORD 기록
ord-4b4211a4ff314f0db042e5e2bdad6622
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557125B2

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