Hydrochloric Acid → 4-Fluoro-6-methyl-1-(4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one hydrochloride

HRID 2061469Notes

Reaction equation

HRID 2061469 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]=[C:4]([CH3:25])[CH:3]=1.[ClH:26]>ClCCl.CO.O1CCOCC1>[ClH:26].[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]=[C:4]([CH3:25])[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 596832531,1-Dimethylethyl 4-(4-fluoro-6-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinecarboxylate

Product 1

HCID 686240254-Fluoro-6-methyl-1-(4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one hydrochloride

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

1,1-Dimethylethyl 4-(4-fluoro-6-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinecarboxylate (˜12.3 mmol, 4.3 g) (D4a) was dissolved in dichloromethane/methanol (50 ml/20 ml) and was treated with HCl (10 eq., 0.123 mol, ˜30 ml of a 4M solution in 1,4-dioxane) at room temperature; the mixture was stirred at room temperature for one overnight. Solvent was evaporated and the solid obtained was triturated with diethyl ether to afford the title compound (3.5 g, about 12.3 mmol brown solid) as the mono hydrochloride salt, M++H=250.

Workup

  1. customSolvent was evaporated
  2. customthe solid obtained
  3. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-4c9c09fdba324ee88678b563ec9ba15d
Source dataset
uspto-grants-2012_10
Patent number
US08283364B2

Reaction notes

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