Benzhydrylamine → 1-(Diphenylmethyl)-3-methylazetidin-3-ol hydrochloride

HRID 1461109Notes

Reaction equation

HRID 1461109 reaction equation
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:8]2[CH2:11][C:10]([OH:13])([CH3:12])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:20]CC1(C)OC1.C1(C(N)C2C=CC=CC=2)C=CC=CC=1>CO>[ClH:20].[C:14]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:11][C:10]([OH:13])([CH3:12])[CH2:9]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 7036BenzhydrylamineHCID 952202-(Chloromethyl)-2-methyloxiraneHCID 102439891-Benzhydryl-3-methylazetidin-3-ol

Product 1

HCID 144051211-(Diphenylmethyl)-3-methylazetidin-3-ol hydrochlorideYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

b,c) 1-Diphenylmethyl-3-hydroxy-3-methylazetidine. 12.5 g (117.3 mmol) of 1-chloro-2,3-epoxy-2-methylpropane are added to a solution of 21.5 g (117.3 mmol) of diphenylmethylamine dissolved in 50 ml of methanol, and the mixture is left for 3 days at room temperature and subsequently for 3 days under reflux. The methanol is evaporated off under reduced pressure, the resulting solid is washed with acetone and filtered off, and 28.8 g (85%) of 1-diphenylmethyl-3-hydroxy-3-methylazetidine hydrochloride, melting point 187°-197° C., are obtained.

Workup

  1. temperatureunder reflux
  2. customThe methanol is evaporated off under reduced pressure
  3. washthe resulting solid is washed with acetone
  4. filtrationfiltered off

Sources & evidence

ORD record
ord-f50176f3c5454427a76be8d85f7dd200
Source dataset
uspto-grants-1991_12
Patent number
US05073646

Reaction notes

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