Sodium Bicarbonate → HCID 22168132, compound

HRID 1031541Notes

Reaction equation

HRID 1031541 reaction equation
C(=O)(O)[O-].[Na+].Cl[CH2:7][CH2:8][CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[NH:12][C:11]1=[O:19].[F:20][C:21]1[C:33]([F:34])=[C:32]([F:35])[C:31]([F:36])=[C:30]([F:37])[C:22]=1[O:23][CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>CN(C)C=O>[O:19]=[C:11]1[N:10]([CH:9]([N:27]2[CH2:26][CH2:25][CH:24]([O:23][C:22]3[C:30]([F:37])=[C:31]([F:36])[C:32]([F:35])=[C:33]([F:34])[C:21]=3[F:20])[CH2:29][CH2:28]2)[CH2:8][CH3:7])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[NH:12]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 18104191-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-oneHCID 148370404-(2,3,4,5,6-Pentafluorophenoxy)piperidine

Product 1

HCID 22168132HCID 22168132, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
75 °C

Procedure

A mixture of 10 g of sodium bicarbonate, 3.58 g of 1-(3-chloropropyl)-1,3-dihydro-2-oxo-2H-benzimidazole and 60 ml of dimethylformamide was treated with a solution of 4.0 g of 4-(2,3,4,5,6-pentafluorophenoxy)piperidine in 20 ml dimethylformamide and stirred at 75° C. for 1.5 hours. The reaction mixture was then cooled and filtered. The filtrate was poured into water and extracted with ethyl acetate. The organic layer was washed with water followed by a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. After filtering, evaporation of the volatiles afforded a residue which was purified by means of high pressure liquid chromatography (silica gel; elution with 5% methanol/dichloromethane). Recrystallization from isopropyl ether afforded 3.6 g (54%) of 1-[1-(1,3-dihydro-2-oxo-2H-benzimidazol-1-yl)propyl]-4-(2,3,4,5,6-pentafluorophenoxy)piperidine, m.p. 117°-120° C.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. filtrationfiltered
  3. additionThe filtrate was poured into water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter filtering
  8. customevaporation of the volatiles
  9. customafforded a residue which
  10. customwas purified by means of high pressure liquid chromatography (silica gel; elution with 5% methanol/dichloromethane)
  11. customRecrystallization from isopropyl ether

Sources & evidence

ORD record
ord-5d2be944ec684cada516f1ce5085d1fd
Source dataset
uspto-grants-1990_09
Patent number
US04954511

Reaction notes

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