Sodium Bicarbonate → HCID 58599520, compound

HRID 2240285Notes

Reaction equation

HRID 2240285 reaction equation
Cl.Cl.[CH2:3]([C:5]1[N:9]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[C:8]2[CH:16]=[CH:17][CH:18]=[CH:19][C:7]=2[N:6]=1)[CH3:4].Cl[CH2:21][CH2:22][CH2:23][S:24]([C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)(=[O:26])=[O:25].C1COCC1.CN(C=O)C.C([O-])(O)=O.[Na+]>O.CN(P(N(C)C)(N(C)C)=O)C>[CH2:3]([C:5]1[N:9]([CH:10]2[CH2:11][CH2:12][N:13]([CH2:21][CH2:22][CH2:23][S:24]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[CH2:14][CH2:15]2)[C:8]2[CH:16]=[CH:17][CH:18]=[CH:19][C:7]=2[N:6]=1)[CH3:4]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 14005906HCID 14005906, compoundHCID 21974620tetrahydrofuran N,N-dimethylformamideHCID 68582975HCID 68582975, compound

Product 1

HCID 58599520HCID 58599520, compoundYield 46.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

To a stirred solution of 2-ethyl-1-piperidin-4-yl-1H-benzimidazole dihydrochloride (3.02 g) and 1-(3-chloropropane-1-sulfonyl)4-fluorobenzene (2.6 g) in 3:1 THF-DMF (25 ml) was added NaHCO3 (2.9 g), KI (0.3 g) and HMPT (5 ml). The mixture was heated at reflux for 2 h, and then allowed to cool to rt. Water (100 ml) was added and the mixture extracted with ethyl acetate (2×80 ml), and the organic layer separated and washed with water. This was further dried and concentrated in vacuo. The oil was purified by flash chromatography and the free base converted to the hydrochloride salt by action of HCl in ethanol. The solid was recrystallised from ethanol-petroleum ether to yield 2.0 g of the title compound as colourless crystals. Mp. 212-216° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. extractionthe mixture extracted with ethyl acetate (2×80 ml)
  4. customthe organic layer separated
  5. washwashed with water
  6. customThis was further dried
  7. concentrationconcentrated in vacuo
  8. customThe oil was purified by flash chromatography
  9. customThe solid was recrystallised from ethanol-petroleum ether

Sources & evidence

ORD record
ord-3ac1c3693f44461bb72e8feb93719b07
Source dataset
uspto-grants-2010_05
Patent number
US07723360B2

Reaction notes

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