Methyl Isobutyl Ketone → 1,3-dihydro-1-(1-methylethenyl)-3-[3-[4-[2-(3-methylphenyl)-2-oxoethyl]-1-piperidinyl]propyl]-2H-benzimidazol-2-one

HRID 126869Notes

Reaction equation

HRID 126869 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:14]([CH3:16])=[CH2:15])[C:6]1=[O:17].Br.[CH3:19][C:20]1[CH:21]=[C:22]([C:26](=[O:34])[CH2:27][CH:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:23]=[CH:24][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+].CC(C)CC(=O)C>O>[CH3:16][C:14]([N:7]1[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:5]([CH2:4][CH2:3][CH2:2][N:31]2[CH2:30][CH2:29][CH:28]([CH2:27][C:26]([C:22]3[CH:23]=[CH:24][CH:25]=[C:20]([CH3:19])[CH:21]=3)=[O:34])[CH2:33][CH2:32]2)[C:6]1=[O:17])=[CH2:15]

Participants

6

Reactant 4

HCID 7909Methyl Isobutyl KetoneHCID 10340Sodium CarbonateHCID 30173591-(3-Chloropropyl)-1,3-dihydro-3-(1-methylvinyl)-2H-benzimidazol-2-oneHCID 20288052HCID 20288052, compound

Product 1

HCID 202880281,3-dihydro-1-(1-methylethenyl)-3-[3-[4-[2-(3-methylphenyl)-2-oxoethyl]-1-piperidinyl]propyl]-2H-benzimidazol-2-oneYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 5.5 parts of 1-(3-chloropropyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one, 6 parts of 1-(3-methylphenyl)-2-(4-piperidinyl)ethanone hydrobromide, 8.5 parts of sodium carbonate and 120 parts of 4-methyl-2-pentanone is stirred and refluxed overnight using a water-separator. The reaction mixture is cooled, water is added and thelayers are separated. The 4-methyl-2-pentanone-phase is dried, filtered and evaporated, yielding 8.6 parts (100%) of 1,3-dihydro-1-(1-methylethenyl)-3-[3-[4-[2-(3-methylphenyl)-2-oxoethyl]-1-piperidinyl]propyl]-2H-benzimidazol-2-one as an oily residue.

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe reaction mixture is cooled
  3. customthelayers are separated
  4. dry with materialThe 4-methyl-2-pentanone-phase is dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-8cedc196c3ce4a83b17bf691c8a66449
Source dataset
uspto-grants-1981_03
Patent number
US04254127

Reaction notes

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