Benzylamine → N-[(Trimethylsilyl)methyl]benzylamine

HRID 233412

반응식

HRID 233412 반응식
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12]>[OH-].[Na+]>[CH3:10][Si:11]([CH2:14][NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH3:13])[CH3:12]

참가 물질

4

반응물 2

HCID 7504BenzylamineHCID 75361Silane, (chloromethyl)trimethyl-

생성물 1

HCID 353458N-[(Trimethylsilyl)methyl]benzylamine수율 81.5%

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매

반응 조건

온도
10 °C

실험 절차

A mixture of 264 mL (2.42 mol) of benzylamine and 97.7 g. (0.796 mol) of chloromethyltrimethylsilane was heated to 200° C. for 2.5 h then cooled to 10° C. A 0.1M sodium hydroxide solution (400 mL) was added and the product was extracted with 3×200 mL of diethyl ether. The combined organic phase was washed with 100 mL of water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The product was distilled at 115°-125° C. and 5 mm of Hg to give 125.4 g (81% yield) of N-trimethylsilylmethyl benzylamine as a clear liquid; 1H NMR (CDCl3) δ:0.0 (s, 9H), 1.1 (br s, 1H), 2.01 (s, 2H), 3.76 (s, 2H), 7.1-7.3 (m, 5H).

후처리

  1. extractionthe product was extracted with 3×200 mL of diethyl ether
  2. washThe combined organic phase was washed with 100 mL of water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. distillationThe product was distilled at 115°-125° C.

출처 및 근거

ORD 기록
ord-eb0f2a6f678f49c99c4671e422325c84
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05591884

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