Hydrochloric Acid → 1,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one

HRID 962742Notes

Reaction equation

HRID 962742 reaction equation
Cl.C(OC([N:9]1[CH2:14][CH2:13][CH:12]([N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17](C)[C:16]2=[O:25])[CH2:11][CH2:10]1)=O)(C)(C)C>C(OCC)(=O)C>[NH:9]1[CH2:10][CH2:11][CH:12]([N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[NH:17][C:16]2=[O:25])[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21222103tert-Butyl 4-(3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidine-1-carboxylate

Product 1

HCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A stream of hydrogen chloride gas was dispersed through a stirred, ice cold solution of 0.383 g of 1,3-dihydro-1-(1-tert-butyloxycarbonylpiperidin-4-yl)-3-methyl-2H-benzimidazol-2-one in 500 mL of ethyl acetate for 30 min. Stirring was continued at 0° C. for 1 h, then at ambient temperature for 1 h. The suspension was partitioned between 250 mL of chloroform and 50 mL of saturated Na2CO3. Drying under reduced pressure gave 0.296 of 1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one as an off-white solid.

Workup

  1. waitat ambient temperature for 1 h
  2. customThe suspension was partitioned between 250 mL of chloroform and 50 mL of saturated Na2CO3
  3. customDrying under reduced pressure

Sources & evidence

ORD record
ord-e889e2145f2549ed9ca18ed4575c0e13
Source dataset
uspto-grants-1998_06
Patent number
US05760054

Reaction notes

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