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

HRID 1518547Notes

Reaction equation

HRID 1518547 reaction equation
[C:1]1([CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:16][CH:17]1[CH2:19][O:18]1>CCO>[CH:7]([N:8]1[CH2:19][CH:17]([OH:18])[CH2:16]1)([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 7036BenzhydrylamineHCID 7835Epichlorohydrin

Product 1

HCID 3304481-(Diphenylmethyl)azetidin-3-olYield 51.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of diphenylmethanamine (16.2 g, 88.5 mmol) and 2-(chloromethyl)oxirane (8.19 g, 88.5 mmol) in dry EtOH was stirred at RT for 48 hours and then heated at reflux for 48 hour. The reaction mixture was concentrated under reduced pressure and the residue was stirred in acetone (300 mL) for 30 min. The resulting off-white solid precipitate was filtered, washed with cold acetone (100 mL), and dried in vacuo to obtain 1-benzhydrylazetidin-3-ol as white crystalline solid (11.0 g, 51% yield); LC-MS: 240.3 (M+H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 48 hour
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. filtrationThe resulting off-white solid precipitate was filtered
  5. washwashed with cold acetone (100 mL)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-bc8726fa54a0420ab4f275487a198338
Source dataset
uspto-grants-2012_07
Patent number
US08232406B2

Reaction notes

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