Benzhydrylamine → 1-Benzhydryl-3-methylazetidin-3-ol

HRID 519208Notes

Reaction equation

HRID 519208 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][C:17]1([CH3:20])[CH2:19][O:18]1>CO>[CH:7]([N:8]1[CH2:19][C:17]([CH3:20])([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 952202-(Chloromethyl)-2-methyloxirane

Product 1

HCID 102439891-Benzhydryl-3-methylazetidin-3-olYield 63.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Diphenylmethanamine (68.8 mL, 375 mmol) was added dropwise into a solution of 2-(chloromethyl)-2-methyloxirane (40 g, 375 mmol) in methanol (160 mL) and the reaction was stirred at rt for 72 h and then at reflux for 20 h. The reaction was cooled to ambient temperature, evaporated in vacuo and suspended in acetone (200 mL). The solid was collected by filtration to give 1-benzhydryl-3-methyl-azetidin-3-ol (60 g, 63%) as a white solid. 1H NMR (DMSO-d6, 400 MHz): δ7.61 (m, 4H), 7.31 (m, 6H), 6.43 (m, 1H), 6.00 (m, 1H), 3.80-4.00 (m, 4H), 1.45 (m, 3H).

Workup

  1. temperatureat reflux for 20 h
  2. temperatureThe reaction was cooled to ambient temperature
  3. customevaporated in vacuo
  4. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-51997035b2594f39aa7eb90a0729c674
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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