Methyl Isobutyl Ketone → HCID 21500290, compound

HRID 1729817Notes

Reaction equation

HRID 1729817 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH:5]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.[Cl:20][C:21]1[C:22]([C:37]([F:40])([F:39])[F:38])=[CH:23][C:24]2[NH:28][C:27](=[O:29])[N:26]([CH:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[C:25]=2[CH:36]=1.C(=O)([O-])[O-].[Na+].[Na+].CC(C)[CH2:49][C:50](=[O:52])[CH3:51]>O>[CH3:49][CH:50]([O-:52])[CH3:51].[Cl:20][C:21]1[C:22]([C:37]([F:40])([F:39])[F:38])=[CH:23][C:24]2[NH:28][C:27](=[O:29])[N:26]([CH:30]3[CH2:31][CH2:32][N:33]([CH2:2][CH2:3][CH2:4][CH:5]([C:13]4[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=4)[C:6]4[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=4)[CH2:34][CH2:35]3)[C:25]=2[CH:36]=1

Participants

6

Reactant 4

HCID 7909Methyl Isobutyl KetoneHCID 10340Sodium CarbonateHCID 768201,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)HCID 21500254HCID 21500254, compound

Product 1

HCID 21500290HCID 21500290, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 3.5 parts of 1-chloro-4,4-bis(4-fluorophenyl)-butane, 2.5 parts of 6-chloro-1,3-dihydro-1-(4-piperidinyl)-5-(trifluoromethyl)-2H-benzimidazol-2-one, 2.65 parts of sodium carbonate and 100 parts of 4-methyl- 2-pentanone is stirred and refluxed overnight 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 solid residue is purified by column-chromatography over silicagel, using a mixture of trichloromethane and 5% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 2-propanol, yielding 6-chloro-1-{1-[4,4-bis(4-fluorophenyl)butyl]-4-piperidinyl}-1,3-dihydro-5-(trifluoromethyl)-2H-benzimidazol-2-one 2-propanolate; mp. 200° C.

Workup

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

Sources & evidence

ORD record
ord-c4e53d36a68b42e0bda85723e2c0a844
Source dataset
uspto-grants-1976_11
Patent number
US03989707

Reaction notes

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