1,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one → HCID 22111089, compound

HRID 565670Notes

Reaction equation

HRID 565670 reaction equation
Br[CH2:2][C:3]1([CH3:16])[CH2:7][C:6]2[C:8]([CH3:15])=[C:9]([NH2:14])[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]=2[O:4]1.[O:17]=[C:18]1[N:22]([CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[C:21]2[CH:29]=[CH:30][CH:31]=[CH:32][C:20]=2[NH:19]1>C1(C)C(C)=CC=CC=1>[O:17]=[C:18]1[N:22]([CH:23]2[CH2:24][CH2:25][N:26]([CH2:2][C:3]3([CH3:16])[CH2:7][C:6]4[C:8]([CH3:15])=[C:9]([NH2:14])[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]=4[O:4]3)[CH2:27][CH2:28]2)[C:21]2[CH:29]=[CH:30][CH:31]=[CH:32][C:20]=2[NH:19]1

Participants

4

Reactant 2

HCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 108505902-Bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine

Product 1

HCID 22111089HCID 22111089, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
180 °C

Procedure

In an autoclave, a suspension of 2-bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine (1.4 g) and 4-(2-keto-1-benzimidazolinyl)piperidine (2.3 g) in xylene (20 mL) was stirred under nitrogen gas at 180° C. for 15 hours. The reaction mixture was then cooled, filtered, and washed with diethyl ether. The filtrate was washed with water and extracted with 1N-hydrochloric acid. The aqueous layer was neutralized with saturated aqueous NaHCO3 and extracted with 2 portions of ethyl acetate. The pooled organic layer was washed with saturated aqueous NaCl, dried over anhydrous sodium sulfate (Na2SO4) and silica gel (eluted with ethyl acetate), and concentrated under reduced pressure. The residue was crystallized from ethanol to give 1.2 g of 2-[[4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]methyl]-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine. Yield 55%. This product was dissolved in tetrahydrofuran with heating and after the solution was diluted with methanol, a stoichiometric excess of 10% HCl/methanol was added. The resulting solution was concentrated under reduced pressure and cyrstallized from methanol/diethyl ether to provide the title compound.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. filtrationfiltered
  3. washwashed with diethyl ether
  4. washThe filtrate was washed with water
  5. extractionextracted with 1N-hydrochloric acid
  6. extractionextracted with 2 portions of ethyl acetate
  7. washThe pooled organic layer was washed with saturated aqueous NaCl
  8. dry with materialdried over anhydrous sodium sulfate (Na2SO4) and silica gel (eluted with ethyl acetate)
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-f755b9f33be047ac8afc11a8e98ff114
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

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