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

HRID 1690364

반응식

HRID 1690364 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 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).

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-bf71ad145d10471695f44ad52635afb5
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153652B2

연결된 노트

불러오는 중…