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

HRID 1582391Notes

Reaction equation

HRID 1582391 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 42%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of benzhydrylamine (25.0 g, 136 mmol), epichlorohydrine (12.6 g, 136 mmol) in MeOH (55 mL) was stirred for 3 days at room temperature. Then the mixture was stirred under reflux for 2 days. After cooling, the solvent was evaporated in vacuo and the resulting solid was washed with acetone (30 mL). Then the solid was suspended in Et2O (500 mL) and washed with aqueous 6N NaOH (100 mL). The organic layer was dried over MgSO4 and concentrated in vacuo to afford a product (13.6 g, 42%). This compound was used for the next reaction without further purification.

Workup

  1. stirringThen the mixture was stirred
  2. temperatureunder reflux for 2 days
  3. temperatureAfter cooling
  4. customthe solvent was evaporated in vacuo
  5. washthe resulting solid was washed with acetone (30 mL)
  6. washwashed with aqueous 6N NaOH (100 mL)
  7. dry with materialThe organic layer was dried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6deaf2dbf7fe448f9a479a9f57b9707a
Source dataset
uspto-grants-2004_05
Patent number
US06734306B2

Reaction notes

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