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

HRID 1457087Notes

Reaction equation

HRID 1457087 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, 1.6 mol) and epichlorohydrin (186 ml, 1 mol equivalent) 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), the combined organic extracts dried over magnesium sulphate, filtered and the solvent evaporated under reduced pressure to give the title product (86 g) as a crystalline solid. 1H-NMR (CDCl3): δ=1.8-2.3(s,br,1H), 2.85-2.9(m,2H), 3.5-3.55(m,2H), 4.35(s,1H), 4.4-4.5(m, 1H), 7.15-7.4(m,10H)ppm.

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 extracts dried over magnesium sulphate
  10. filtrationfiltered
  11. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-42e23096f3ef4c698824ae3e268f047c
Source dataset
uspto-grants-1998_12
Patent number
US05846965

Reaction notes

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