Benzylamine → N-[(Trimethylsilyl)methyl]benzylamine

HRID 233412

反応式

HRID 233412 の反応式
[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]

参加物

4

反応物 2

HCID 7504BenzylamineHCID 75361Silane, (chloromethyl)trimethyl-

生成物 1

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

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒

反応条件

温度
10 °C

実験手順

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).

後処理

  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.

出典と根拠

ORDレコード
ord-eb0f2a6f678f49c99c4671e422325c84
出典データセット
uspto-grants-1997_01
特許番号
US05591884

関連ノート

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