Hydrochloric Acid → 1-(azetidin-3-yl)-1H-1,2,3-triazole hydrochloride

HRID 1742995Notes

Reaction equation

HRID 1742995 reaction equation
C([N:14]1[CH2:17][CH:16]([N:18]2[CH:22]=[CH:21][N:20]=[N:19]2)[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.[ClH:23]>C(O)C.[Pd]>[ClH:23].[N:18]1([CH:16]2[CH2:17][NH:14][CH2:15]2)[CH:22]=[CH:21][N:20]=[N:19]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 54270435N-Benzhydryl-3-(1,2,3-triazol-1-yl) azetidine

Product 1

HCID 190059921-(azetidin-3-yl)-1H-1,2,3-triazole hydrochlorideYield 51%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 0.88 g (3.03 mmol) of N-benzhydryl-3-(1,2,3-triazol-1-yl) azetidine in 25 ml of 98% ethanol was added 3 ml of 1N hydrochloric acid. To this solution was added 0.3 g of Pd/C (10%) and the mixture was then hydrogenated at 50 psi for 18 hr. After filtration of the Pd/C the solvent was removed under reduced pressure, and the residue was crystallized from methanol-ether to yield 0.25 g (51%) of the desired product m.p. 158°-160° C. 1H NMR (D2O) 6 8.16 (S, 1H), 7.92 (S, 1H), 5.95-5.75 (m, 1H), 4.97-4.65 (m, 4H).

Workup

  1. filtrationAfter filtration of the Pd/C the solvent
  2. customwas removed under reduced pressure
  3. customthe residue was crystallized from methanol-ether

Sources & evidence

ORD record
ord-30fdee44935e436ea2daf8d1e0abbcd0
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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