Sodium Hydroxide → N1-Cyclopentylpropane-1,3-diamine

HRID 1776252ノート

反応式

HRID 1776252 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([NH:12][CH2:13][CH2:14][C:15]#[N:16])[CH2:11][CH2:10][CH2:9][CH2:8]1.[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>C(OCC)C.O>[CH:7]1([NH:12][CH2:13][CH2:14][CH2:15][NH2:16])[CH2:11][CH2:10][CH2:9][CH2:8]1

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 27580023-(Cyclopentylamino)propionitrileHCID 21226445Aluminium lithium hydride

生成物 1

HCID 19963439N1-Cyclopentylpropane-1,3-diamine収率 73%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 3283Diethyl Ether溶媒2 回

実験手順

To a cooled (0° C.) suspension of lithium aluminum hydride (3.295 g, 86.8 mmol) in anhydrous diethyl ether (150 mL) was added a solution of 3-(cyclopentylamino)propanenitrile (6.000 g, 43.4 mmol) in anhydrous diethyl ether (40 mL), dropwise over 45 mins. The reaction mixture was stirred at room temperature for 15 mins and at reflux for 4 hrs, cooled to room temperature and stirred for 1 hr. The mixture was cooled to 0° C. and vigorously stirred while water (3.4 mL) was added dropwise, followed by 15% aqueous sodium hydroxide (3.4 mL), and finally water (10.2 mL). The resultant slurry was warmed to room temperature, stirred for 15 mins, and anhydrous magnesium sulfate was added, stirring for an additional 15 mins. Solid materials were removed by filtration, washing multiple times with warm methylene chloride, and the filtrate concentrated under reduced pressure to give the desired product as a clear oil (4.5 g, 73%). 1H NMR (CDCl3, 300 MHz) δ 3.05-2.96 (quint, 1H, J=6.6 Hz), 2.74-2.71 (t, 2H, J=6.6 Hz), 2.68-2.58 (t, 2H, J=6.9 Hz), 1.85-1.68 (m, 2H), 1.62-1.42 (m, 6H), 1.34 (br s, 3H), 1.30-1.21 (m, 2H).

後処理

  1. temperatureTo a cooled
  2. temperatureat reflux for 4 hrs
  3. temperaturecooled to room temperature
  4. stirringstirred for 1 hr
  5. temperatureThe mixture was cooled to 0° C.
  6. additionwas added dropwise
  7. temperatureThe resultant slurry was warmed to room temperature
  8. stirringstirred for 15 mins
  9. stirringstirring for an additional 15 mins
  10. customSolid materials were removed by filtration
  11. washwashing multiple times with warm methylene chloride
  12. concentrationthe filtrate concentrated under reduced pressure

出典と根拠

ORDレコード
ord-4c284a81b7ab42dcb6e6d09df7f40557
出典データセット
uspto-grants-2016_02
特許番号
US09265772B2

反応ノート

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