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

HRID 1066062Notes

Reaction equation

HRID 1066062 reaction equation
[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

Participants

4

Reactant 2

HCID 7036BenzhydrylamineHCID 7835Epichlorohydrin

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

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 five days and then heated at 40° C. for two days. The solvent was then removed under reduced pressure, the residue dissolved in isopropyl alcohol (500 ml) and the solution heated under reflux for six hours. The solution was cooled to room temperature and the precipitate filtered off. This solid was partitioned between dichloromethane (400 ml) and saturated aqueous sodium bicarbonate solution (500 ml). The aqueous phase was extracted with dichloromethane (2×400 ml) and the combined organic phases dried over magnesium sulphate. The solution was then filtered and the solvent removed from the filtrate under reduced pressure to give the title compound (86 g) as a crystalline solid.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. dissolutionthe residue dissolved in isopropyl alcohol (500 ml)
  3. temperaturethe solution heated
  4. temperatureunder reflux for six hours
  5. temperatureThe solution was cooled to room temperature
  6. filtrationthe precipitate filtered off
  7. customThis solid was partitioned between dichloromethane (400 ml) and saturated aqueous sodium bicarbonate solution (500 ml)
  8. extractionThe aqueous phase was extracted with dichloromethane (2×400 ml)
  9. dry with materialthe combined organic phases dried over magnesium sulphate
  10. filtrationThe solution was then filtered
  11. customthe solvent removed from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-0a0f79c64dfa40c1be57522fe94ca764
Source dataset
uspto-grants-2001_06
Patent number
US06242438B1

Reaction notes

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