Hydrochloric Acid → 4-fluoro-1-(piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one hydrochloride

HRID 2378969Notes

Reaction equation

HRID 2378969 reaction equation
[F:1][C:2]1[C:10]2[NH:9][C:8](=[O:11])[N:7]([CH:12]3[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[ClH:25].O1CCOCC1>ClCCl>[ClH:25].[F:1][C:2]1[C:10]2[NH:9][C:8](=[O:11])[N:7]([CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59006349tert-butyl 4-(4-fluoro-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidine-1-carboxylate

Product 1

HCID 689638974-fluoro-1-(piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(4-fluoro-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidine-1-carboxylate (1.03 g, 3.07 mmol) was dissolved in dichloromethane (30 ml). 4N Hydrogen chloride in 1,4-dioxane (8 ml, 32 mmol) was added to the reaction at room temperature. The reaction stirred at room temperature for 5 hours. The solvent was removed in vacuo. Title compound was obtained as white solid in quantitative yield. 1H NMR (400 MHz, MeOD) δ ppm 7.14 (d, J=8.81 Hz, 1 H) 7.00-7.10 (m, 1 H) 6.80-6.92 (m, 1 H) 4.48-4.63 (m, 1 H) 3.52-3.60 (m, 2 H) 3.16-3.26 (m, 2 H) 2.64-2.82 (m, 2 H) 2.04 (dd, J=12.46, 1.89 Hz, 2 H).

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-38d3d0ca9c2045048eac99364c31e069
Source dataset
uspto-grants-2008_12
Patent number
US07470680B2

Reaction notes

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