Hydrochloric Acid → HCID 66785056, compound

HRID 1096598Notes

Reaction equation

HRID 1096598 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[C@@H:15]1[CH2:20][CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16]1.Cl>CCO>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[C@@H:15]1[CH2:20][CH2:19][CH2:18][NH:17][CH2:16]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66786343(R)-tert-butyl 3-(1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidine-1-carboxylate

Product 1

HCID 66785056HCID 66785056, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-tert-Butyl 3-(1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidine-1-carboxylate (4.82 mmol; 1.8 g) was added to a 100 mL round-bottomed flask equipped with a reflux condenser and stirring under nitrogen. EtOH (15 mL) and HCl (8 M in H2O; 4 mL) were then added and the solution was heated to reflux for 10 min. Analysis of the reaction mixture by LC/MS indicated that the reaction was complete. The solvent was then removed in-vacuo. The resultant oil was then extracted with EtOAc and a 10% aqueous K2CO3 solution. The organic layer was collected and dried with Na2SO4, and was then filtered. The filtrate was concentrated and dried in-vacuo affording (R)-1-(3-methoxypropyl)-2-(piperidin-3-yl)-1H-benzo[d]imidazole (7D) as a brown oil (4.76 mmol, 1.3 g, 99% yield). ESI-MS: m/z 274.4 (M+H)+.

Workup

  1. customequipped with a reflux condenser
  2. temperaturethe solution was heated
  3. temperatureto reflux for 10 min
  4. customThe solvent was then removed in-vacuo
  5. extractionThe resultant oil was then extracted with EtOAc
  6. customThe organic layer was collected
  7. dry with materialdried with Na2SO4
  8. filtrationwas then filtered
  9. concentrationThe filtrate was concentrated
  10. customdried in-vacuo

Sources & evidence

ORD record
ord-85b5fcc0fc0040f2a73f811adea3dee8
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

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