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

HRID 1067901

반응식

HRID 1067901 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 67553Tetrabutylammonium Iodide촉매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2e6182b2560f49de91847f7ddb264d2c
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06248885B1

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