O-ethylhydroxylamine hydrochloride → 5-Acetyl-1-[3-(1-methyl-1,2,3,6-tetrahydropyrid-5-yl)phenyl]benzimidazole O-ethyl oxime

HRID 324735Notes

Reaction equation

HRID 324735 reaction equation
[C:1]([C:4]1[CH:25]=[CH:24][C:7]2[N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17]4[CH2:22][N:21]([CH3:23])[CH2:20][CH2:19][CH:18]=4)[CH:12]=3)[CH:9]=[N:10][C:6]=2[CH:5]=1)(=O)[CH3:2].Cl.[CH2:27]([O:29][NH2:30])[CH3:28]>C(O)C>[CH2:27]([O:29][N:30]=[C:1]([C:4]1[CH:25]=[CH:24][C:7]2[N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17]4[CH2:22][N:21]([CH3:23])[CH2:20][CH2:19][CH:18]=4)[CH:12]=3)[CH:9]=[N:10][C:6]=2[CH:5]=1)[CH3:2])[CH3:28]

Participants

4

Reactant 2

HCID 76850O-ethylhydroxylamine hydrochlorideHCID 227419115-Acetyl-1-[3-(1-methyl-1,2,3,6-tetrahydropyrid-5-yl)phenyl]benzimidazole

Product 1

HCID 739941495-Acetyl-1-[3-(1-methyl-1,2,3,6-tetrahydropyrid-5-yl)phenyl]benzimidazole O-ethyl oxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-acetyl-1-[3-(1-methyl-1,2,3,6-tetrahydropyrid-5-yl)phenyl]benzimidazole (7) (free base from above) in ethanol was added O-ethyl hydroxylamine hydrochloride. The mixture was heated to reflux for 1.5 hours whereafter the solvent was removed under reduced pressure. The residue was triturated with a mixture of diethyl ether and ethanol leaving 5-acetyl-1-[3-(1-methyl-1,2,3,6-tetrahydropyrid-5-yl)phenyl]benzimidazole O-ethyl oxime (3f8) as hygroscopic crystals. Mp 138-143° C., m/e 374.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1.5 hours whereafter the solvent
  3. customwas removed under reduced pressure
  4. customThe residue was triturated with a mixture of diethyl ether and ethanol

Sources & evidence

ORD record
ord-b237e0607c934edf8faefd1c54182d08
Source dataset
uspto-grants-2001_04
Patent number
US06218547B1

Reaction notes

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