1-Phenylcyclopropanecarbonitrile → 1-Phenylcyclopropanemethanamine

HRID 74747ノート

反応式

HRID 74747 の反応式
[C:1]1([C:7]2([C:10]#[N:11])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:1]1([C:7]2([CH2:10][NH2:11])[CH2:8][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

4

反応物 2

HCID 702881-PhenylcyclopropanecarbonitrileHCID 21226445Aluminium lithium hydride

生成物 1

HCID 702871-Phenylcyclopropanemethanamine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of 1-phenylcyclopropanecarbonitrile (50 g, 0.34 mol, 1 eq.) in tetrahydrofuran (500 mL, 0.7 M) at 0° C. was added lithium aluminum hydride (23 g, 0.35 mol, 1.03 eq.). The reaction mixture was stirred at 0° C. for one hour and then at reflux for one hour. The reaction mixture was then cooled down and quenched with water (23 mL) and a 15% aqueous sodium hydroxide solution (69 mL). The mixture was filtered and concentrated in vacuo to afford #*1 (36 g, 72%). LC-MS: m/z 148.1 [M+H+], retention time=0.86 minutes; 1H NMR (400 MHz, CDCl3) δ 7.2-7.4 (m, 5H), 2.78 (s, 2H), 1.19 (br s, 2H), 0.72-0.84 (m, 4H).

後処理

  1. temperatureat reflux for one hour
  2. temperatureThe reaction mixture was then cooled down
  3. customquenched with water (23 mL)
  4. filtrationThe mixture was filtered
  5. concentrationconcentrated in vacuo
  6. customto afford #*1 (36 g, 72%)

出典と根拠

ORDレコード
ord-38f440307c9f4c8baf1bb6fa411de794
出典データセット
uspto-grants-2014_09
特許番号
US08828401B2

反応ノート

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