Tert-Butylamine → N-tert-butyl-2-methylpropan-1-amine

HRID 1067901

反応式

HRID 1067901 の反応式
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[CH2:6](Br)[CH:7]([CH3:9])[CH3:8].C(#N)CCCCC#N.[OH-].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([NH:5][CH2:6][CH:7]([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 6385Tert-ButylamineHCID 65551-Bromo-2-methylpropaneHCID 8128AdiponitrileHCID 14797Potassium Hydroxide

生成物 1

HCID 527145N-tert-butyl-2-methylpropan-1-amine

試薬・触媒・溶媒 1

HCID 67553Tetrabutylammonium Iodide触媒

実験手順

A mixture of tert-butylamine (10.97 g, 0.15 mol), isobutyl bromide (13.70 g, 0.1 mol), adiponitrile (10.81 g, 0.1 mol) and tetrabutylammonium iodide (1.85 g, 5 mmol) was refluxed with stirring for 12 hours. Aqueous 5 M potassium hydroxide (30 ml, 0.15 mmol) was added and the mixture was extracted with n-pentane (2×50 ml). Three layers were formed. Adiponitrile (the middle layer) was recovered. The pentane solution was dried over anhydrous magnesium sulfate and the product was isolated by distillation to yield 9.5 g, (74%), bp 45-47° C./40 mm Hg; 1H NMR (CDCl3) δ0.91 (d, J=6.5 Hz, 6H, CH3), 1.08 (s, 9H, CH3), 1.64 (sep, J=6.5 Hz, 1H, CH), 2.34 (d, J=6.5 Hz, 2H, CH2).

後処理

  1. temperaturewas refluxed
  2. extractionthe mixture was extracted with n-pentane (2×50 ml)
  3. customThree layers were formed
  4. customAdiponitrile (the middle layer) was recovered
  5. dry with materialThe pentane solution was dried over anhydrous magnesium sulfate
  6. customthe product was isolated by distillation
  7. customto yield 9.5 g, (74%), bp 45-47° C./40 mm Hg

出典と根拠

ORDレコード
ord-2e6182b2560f49de91847f7ddb264d2c
出典データセット
uspto-grants-2001_06
特許番号
US06248885B1

関連ノート

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