Sodium Hydroxide → (1-Phenylcyclobutyl)methanamine

HRID 274117

반응식

HRID 274117 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].C1(C)C=CC=CC=1.C1COCC1.[C:19]1([C:25]2([C:29]#[N:30])[CH2:28][CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-].[Na+]>C1COCC1.O>[C:19]1([C:25]2([CH2:29][NH2:30])[CH2:28][CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 844001-PhenylcyclobutanecarbonitrileHCID 21226445Aluminium lithium hydrideHCID 22635083Tetrahydrofuran toluene

생성물 1

HCID 15611176(1-Phenylcyclobutyl)methanamine수율 81.3%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

A commercial suspension of LiAlH4 at 13% in a toluene-THF mixture, under nitrogen (0.595 mole; 175 ml), diluted with 270 ml of THF is maintained at 0° C. A mixture of 90 g (0.572 mole) of 1-phenylcyclobutanecarbonitrile and 800 ml of THF is added dropwise during 20 minutes. After the addition, the temperature is slowly allowed to rise before heating to reflux during 1 hour. After cooling at about 5° C., 150 ml water, 150 ml 10% NaOH and again 560 ml water are poured dropwise with care. The mixture is extracted with ethyl acetate after having saturated the aqueous phase with NaCl. The organic phase is extracted with a N HCl solution. This aqueous phase is made basic by means of 30% NaOH and is extracted with dichloromethane, which, after washing with water, drying over Na2SO4 and concentration gives a reddish liquid which is purified by distillation. There is obtained 68.65 g (yield=81.3%) of a colorless liquid. b.p.6 =84°-92° C.

후처리

  1. additionis added dropwise during 20 minutes
  2. additionAfter the addition
  3. temperaturebefore heating
  4. temperatureto reflux during 1 hour
  5. temperatureAfter cooling at about 5° C.
  6. extractionThe mixture is extracted with ethyl acetate
  7. extractionThe organic phase is extracted with a N HCl solution
  8. extractionis extracted with dichloromethane, which
  9. washafter washing with water
  10. dry with materialdrying over Na2SO4 and concentration
  11. customgives a reddish liquid which
  12. distillationis purified by distillation

출처 및 근거

ORD 기록
ord-c8121af101cd4bedb07b9546dd5c568e
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05387709

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