Benzhydrylamine → 1-(Diphenylmethyl)azetidin-3-ol

HRID 377026노트

반응식

HRID 377026 반응식
[CH:1]([NH2:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]([CH:17]1[O:19][CH2:18]1)Cl>CO>[C:2]1([CH:1]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:14]2[CH2:18][CH:17]([OH:19])[CH2:15]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 7036BenzhydrylamineHCID 7835Epichlorohydrin

생성물 1

HCID 3304481-(Diphenylmethyl)azetidin-3-ol수율 35.9%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
40 °C

실험 절차

A solution of benzhydrylamine (200 ml, 1.16 mol) and epichlorohydrin (186 ml, 1 mol equiv) in methanol (600 ml) was stirred at room temperature for 5 days and then heated to 40° C. for 2 days. The solvent was then removed in vacuo, the residue dissolved in isopropyl alcohol (500 ml) and the solution heated under reflux for 6 hours. The solution was cooled to room temperature and the precipitate filtered off. The solid was partitioned between dichloromethane (400 ml) and saturated NaHCO3 solution (500 ml). The aqueous phase was extracted with dichloromethane (2×400 ml) and the combined organic phases dried over anhydrous MgSO4. The solvent was then removed in vacuo to give the title compound (86 g) as a crystalline solid.

후처리

  1. customThe solvent was then removed in vacuo
  2. dissolutionthe residue dissolved in isopropyl alcohol (500 ml)
  3. temperaturethe solution heated
  4. temperatureunder reflux for 6 hours
  5. temperatureThe solution was cooled to room temperature
  6. filtrationthe precipitate filtered off
  7. customThe solid was partitioned between dichloromethane (400 ml) and saturated NaHCO3 solution (500 ml)
  8. extractionThe aqueous phase was extracted with dichloromethane (2×400 ml)
  9. dry with materialthe combined organic phases dried over anhydrous MgSO4
  10. customThe solvent was then removed in vacuo

출처 및 근거

ORD 기록
ord-971891d6d27a409dad9f43e466fdf463
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06022971

반응 노트

불러오는 중…