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

HRID 2202603Notes

Reaction equation

HRID 2202603 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>[CH:1]([N:14]1[CH2:18][CH:17]([OH:19])[CH2:15]1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[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 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Benzhydrylamine (12 g, 64 mmol), epichlorohydrin (5.9 g, 64 mmol), and 30 mL of methanol were stored under argon in a light-shielded state for 3 days. Next, the mixture was heated under reflux for 3 days in an oil bath. After the completion of the reaction was confirmed by TLC, the solvent was distilled off. To the resulting residue was added acetone, and the mixture was filtrated. The matter separated by filtration was dissolved in ether and washed with a 6-N sodium hydroxide aqueous solution. The organic layer was dried over sodium sulfate, the solvent was distilled off. Thus the title compound (1.3 g, 83%) was obtained.

Workup

  1. temperatureNext, the mixture was heated
  2. temperatureunder reflux for 3 days in an oil bath
  3. distillationthe solvent was distilled off
  4. additionTo the resulting residue was added acetone
  5. filtrationthe mixture was filtrated
  6. customThe matter separated by filtration
  7. dissolutionwas dissolved in ether
  8. washwashed with a 6-N sodium hydroxide aqueous solution
  9. dry with materialThe organic layer was dried over sodium sulfate
  10. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-08592bbf4cb8462cb34ed0c973f8d3ca
Source dataset
uspto-grants-2016_06
Patent number
US09365553B2

Reaction notes

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