Methyl Isobutyl Ketone → HCID 86734139, compound

HRID 1729811Notes

Reaction equation

HRID 1729811 reaction equation
ClCCCC(C1C=CC(F)=CC=1)C1C=CC(F)=CC=1.Cl[C:21]1[C:36](Cl)=[CH:35][C:24]2[N:25](C3CCNCC3)[C:26](=[O:28])[NH:27][C:23]=2[CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+].CC(C)[CH2:46][C:47](=[O:49])[CH3:48]>O>[CH3:46][CH:47]([O-:49])[CH3:48].[NH:25]1[C:24]2[CH:35]=[CH:36][CH:21]=[CH:22][C:23]=2[NH:27][C:26]1=[O:28]

Participants

6

Reactant 4

HCID 7909Methyl Isobutyl KetoneHCID 10340Sodium CarbonateHCID 768201,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)HCID 13792106HCID 13792106, compound

Product 1

HCID 86734139HCID 86734139, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 7 parts of 1-chloro-4,4-bis(4-fluorophenyl)-butane, 5.75 parts of 5,6-dichloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one, 8 parts of sodium carbonate and 100 parts of 4-methyl-2-pentanone is stirred and refluxed for 12 hours with water-separator. The reaction mixture is cooled to room temperature and water is added. The organic layer is separated, dried, filtered and evaporated. The oily residue is purified by column-chromatography over silicagel, using a mixture of trichloromethane and 10% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The solid residue is crystallized successively: once from 4-methyl-2-pentanone and twice from 2-propanol, yielding 5,6-dichloro-1{1-8 4,4-bis(4-fluorophenyl)butyl]-4-piperidinyl}-1,3 -dihydro-2H-benzimidazol-2-one 2-propanolate; mp. 182.5-184.2° C.

Workup

  1. customThe organic layer is separated
  2. customdried
  3. filtrationfiltered
  4. customevaporated
  5. customThe oily residue is purified by column-chromatography over silicagel
  6. additiona mixture of trichloromethane and 10% of methanol as eluent
  7. customThe pure fractions are collected
  8. customthe eluent is evaporated
  9. customThe solid residue is crystallized successively

Sources & evidence

ORD record
ord-3f7ae42978da4ba688a1f711dad38d69
Source dataset
uspto-grants-1976_11
Patent number
US03989707

Reaction notes

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