Benzhydrylamine → 1-benzhydrylazetidin-3-ol Hydrochloride

HRID 2421292Notes

Reaction equation

HRID 2421292 reaction equation
[NH2:1][CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:15]([CH:17]1[O:19][CH2:18]1)[Cl:16]>CO>[ClH:16].[C:9]1([CH:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[N:1]2[CH2:18][CH:17]([OH:19])[CH2:15]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 7036BenzhydrylamineHCID 7835Epichlorohydrin

Product 1

HCID 28017261-benzhydrylazetidin-3-ol HydrochlorideYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Aminodiphenylmethane (55 g; 0.3 mol) and epichlorhydrin (23.5 ml; 0.3 mol) are mixed in methanol (200 ml). The mixture is heated under reflux for 5 days. The methanol is then evaporated off in order to produce a beige solid. The latter is filtered and washed with ether in order to produce a white solid with a yield of 45%. Melting point: 186.0-186.4° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 5 days
  3. customThe methanol is then evaporated off in order
  4. customto produce a beige solid
  5. filtrationThe latter is filtered
  6. washwashed with ether in order
  7. customto produce a white solid with a yield of 45%

Sources & evidence

ORD record
ord-582fa8042f544650b31885e0a2ea74c8
Source dataset
uspto-grants-2011_06
Patent number
US07956075B2

Reaction notes

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