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

HRID 12482

반응식

HRID 12482 반응식
[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

참가 물질

4

반응물 2

HCID 5445611,1-CyclohexanedicarbonitrileHCID 21226445Aluminium lithium hydride

생성물 1

HCID 71994[1-(Aminomethyl)cyclohexyl]methanamine

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-fb00120b424c46bd9458335a138b45b6
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728018B2

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