Hydrochloric Acid → HCID 59850215, compound

HRID 2064151Notes

Reaction equation

HRID 2064151 reaction equation
[F:1][C:2]1[C:24]([Br:25])=[CH:23][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.Cl>C(O)C>[F:1][C:2]1[C:24]([Br:25])=[CH:23][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59850132HCID 59850132, compound

Product 1

HCID 59850215HCID 59850215, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 1,1-dimethylethyl 4-(5-fluoro-6-bromo-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinecarboxylate (D45) (0.54 g, 1.3 mmole) and 6N HCl (1 ml) in ethanol (15 ml) was heated to reflux temperature for 4 hrs. The mixture was concentrated to dryness under vacuum and the residue treated with aq. sodium carbonate and extracted with ethyl acetate. The organic extract was dried (MgSO4) and concentrated to dryness under vacuum to afford the title compound as pale buff powder, 0.35 g, 85%. LC/MS—92% 314/316 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux temperature for 4 hrs
  3. concentrationThe mixture was concentrated to dryness under vacuum
  4. additionthe residue treated with aq. sodium carbonate
  5. extractionextracted with ethyl acetate
  6. extractionThe organic extract
  7. dry with materialwas dried (MgSO4)
  8. concentrationconcentrated to dryness under vacuum

Sources & evidence

ORD record
ord-285ad87930fb4da48fb6893a5aa0302d
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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