1,1-Dicyanocyclopentane → 1,1-Cyclopentanedimethanamine

HRID 12479

反応式

HRID 12479 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([C:14]#[N:15])([C:12]#[N:13])[CH2:11][CH2:10][CH2:9][CH2:8]1>CCOCC>[NH2:13][CH2:12][C:7]1([CH2:14][NH2:15])[CH2:11][CH2:10][CH2:9][CH2:8]1

参加物

4

反応物 2

HCID 151720351,1-DicyanocyclopentaneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 4325931,1-Cyclopentanedimethanamine

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

A suspension of LiAlH4 (4.74 g) in dry Et2O (100 mL) was cooled in an ice bath, and a solution of cyclopentane-1,1-dicarbonitrile (5.0 g) in Et2O (50 mL) was added dropwise at such a rate that the temperature was kept below 20° C. The mixture was stirred overnight at room temperature, cooled in an ice bath, and quenched by adding H2O (5 mL), 2M aqueous NaOH (10 mL) and again H2O (5 mL). The suspension was filtered, the filter cake was washed with Et2O, and the combined filtrates were evaporated to dryness under reduced pressure to give 4.95 g of a clear, colorless liquid. 1H NMR (400 MHz, CDCl3) δ 1.24 (br s, 4H), 1.22-1.40 (m, 4H), 1.55-1.64 (m, 4H), 2.62 (s, 4H).

後処理

  1. temperaturewas cooled in an ice bath
  2. customwas kept below 20° C
  3. temperaturecooled in an ice bath
  4. customquenched
  5. additionby adding H2O (5 mL), 2M aqueous NaOH (10 mL) and again H2O (5 mL)
  6. filtrationThe suspension was filtered
  7. washthe filter cake was washed with Et2O
  8. customthe combined filtrates were evaporated to dryness under reduced pressure
  9. customto give 4.95 g of a clear, colorless liquid

出典と根拠

ORDレコード
ord-1fe459bff36d43cdb7b880e57236a9c8
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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