Hydrochloric Acid → 1-Benzhydryl-3-hydrazinylazetidine dihydrochloride

HRID 1402024Notes

Reaction equation

HRID 1402024 reaction equation
[C:1]1([CH:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:8]2[CH2:11][CH:10]([NH:12][NH:13]C(OC(C)(C)C)=O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:27]>O1CCOCC1>[ClH:27].[ClH:27].[C:21]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]2[CH2:11][CH:10]([NH:12][NH2:13])[CH2:9]2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59436626Tert-butyl 2-(1-benzhydrylazetidin-3-yl)hydrazinecarboxylate

Product 1

HCID 601459041-Benzhydryl-3-hydrazinylazetidine dihydrochlorideYield 85%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred suspension of tert-butyl 2-[1-(diphenylmethyl)azetidin-3-yl]hydrazinecarboxylate (Preparation 691, 19.3 g, 54.6 mmol) in 1,4-dioxane (64 ml) was added 4M hydrogen chloride in 1,4-dioxane (290 ml) at 0° C. and stirred at room temperature for 4 hours. Then the reaction mixture was concentrated in vacuo and the residue was triturated with diethyl ether to give 15 g (85%) of the title compound as a white solid.

Workup

  1. concentrationThen the reaction mixture was concentrated in vacuo
  2. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-b768fdbbeee1489e8d79030f9140189d
Source dataset
uspto-grants-2014_12
Patent number
US08907101B2

Reaction notes

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