1,1-Cyclohexanedicarbonitrile → [1-(Aminomethyl)cyclohexyl]methanamine

HRID 12482

反応式

HRID 12482 の反応式
[C:1]1([C:9]#[N:10])([C:7]#[N:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[NH2:8][CH2:7][C:1]1([CH2:9][NH2:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

4

反応物 2

HCID 5445611,1-CyclohexanedicarbonitrileHCID 21226445Aluminium lithium hydride

生成物 1

HCID 71994[1-(Aminomethyl)cyclohexyl]methanamine

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

Cyclohexane-1,1-dicarbonitrile (20.0 g) was taken up in dry Et2 (70 mL). This mixture was added dropwise to a suspension of LiAlH4 (17.0 g) in dry Et2O (250 mL) cooled in an ice bath. The mixture was stirred overnight at room temperature, cooled in an ice bath, and quenched by adding H2O (17.0 mL), 2M aqueous NaOH (34.0 mL) and again H2O (17 mL). The suspension was filtered, the filter cake was washed with Et2O, and the combined filtrates were evaporated to dryness yielding 20.8 g of a clear, colorless liquid. 1H NMR (400 MHz, CDCl3) δ 1.05-1.55 (m, 14H), 2.61 (s, 4H).

後処理

  1. temperaturecooled in an ice bath
  2. temperaturecooled in an ice bath
  3. customquenched
  4. additionby adding H2O (17.0 mL), 2M aqueous NaOH (34.0 mL) and again H2O (17 mL)
  5. filtrationThe suspension was filtered
  6. washthe filter cake was washed with Et2O
  7. customthe combined filtrates were evaporated to dryness
  8. customyielding 20.8 g of a clear, colorless liquid

出典と根拠

ORDレコード
ord-fb00120b424c46bd9458335a138b45b6
出典データセット
uspto-grants-2010_06
特許番号
US07728018B2

関連ノート

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