Hydrochloric Acid → HCID 178423463, compound

HRID 1842488Notes

Reaction equation

HRID 1842488 reaction equation
[CH3:1][C:2]1[CH:21]=[CH:20][C:5]2[NH:6][C:7]([CH:9]3[CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]3)=[N:8][C:4]=2[CH:3]=1.[ClH:22]>O1CCOCC1>[ClH:22].[ClH:22].[NH:11]1[CH2:12][CH:9]([C:7]2[NH:6][C:5]3[CH:20]=[CH:21][C:2]([CH3:1])=[CH:3][C:4]=3[N:8]=2)[CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178423469HCID 178423469, compound

Product 1

HCID 178423463HCID 178423463, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To tert-butyl 3-(5-methyl-1H-benzo[d]imidazol-2-yl)azetidine-1-carboxylate (prepared in the previous step) was added 4 M HCl in dioxane (30 mL). The reaction mixture was stirred at RT. After 30 min, a solid coated the inside of the flask. The liquid was removed from the flask and the remaining solid was dried under high vacuum. The solid was dissolved in MeOH (20 mL) and diluted with ether (50 mL). The precipitate was collected by filtration and dried under high vacuum to give 2-(azetidin-3-yl)-5-methyl-1H-benzo[d]imidazole dihydrochloride (2.99 g, 11.5 mmol 84% yield over three steps) as a dark red solid.

Workup

  1. customThe liquid was removed from the flask
  2. customthe remaining solid was dried under high vacuum
  3. dissolutionThe solid was dissolved in MeOH (20 mL)
  4. additiondiluted with ether (50 mL)
  5. filtrationThe precipitate was collected by filtration
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-3d6aaac42ba24692be9c8ed865f5f89e
Source dataset
uspto-grants-2015_02
Patent number
US08946230B2

Reaction notes

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