Water → 1-(1-Benzyl-piperidin-4-yl)-2-ethyl-5-fluoro-1H-benzimidazole

HRID 2240279Notes

Reaction equation

HRID 2240279 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[NH:22][C:23](=O)[CH2:24][CH3:25])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C([O-])([O-])=O.[K+].[K+]>C(O)(=O)C.C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=3[N:22]=[C:23]2[CH2:24][CH3:25])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 58599525N-[2-(1-Benzyl-piperidin-4-ylamino)-5-fluorophenyl]-propionamide

Product 1

HCID 585995231-(1-Benzyl-piperidin-4-yl)-2-ethyl-5-fluoro-1H-benzimidazoleYield 96.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-[2-(1-Benzyl-piperidin-4-ylamino)-5-fluorophenyl]-propionamide (7 g) in glacial acetic acid (70 ml) was heated at reflux for 1 h. After cooling the residue was dissolved in ethyl acetate (100 ml) and water (50 ml) was then added. The mixture was made alkaline with K2CO3, and the organic layer separated, washed with water, then dried and concentrated in vacuo. The resulting oil was purified by flash chromatography (9:1 DCM:MeOH) to yield 6.4 g of the title compound.

Workup

  1. temperatureat reflux for 1 h
  2. temperatureAfter cooling the residue
  3. customthe organic layer separated
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe resulting oil was purified by flash chromatography (9:1 DCM:MeOH)

Sources & evidence

ORD record
ord-b201cda3cc8045d3a216e54b68885b0e
Source dataset
uspto-grants-2010_05
Patent number
US07723360B2

Reaction notes

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