Hydroxide → HCID 68139461, compound

HRID 1729825Notes

Reaction equation

HRID 1729825 reaction equation
[Cl:1][C:2]1[CH:35]=[CH:34][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH:19]([C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=4)[C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)[CH2:12][CH2:11]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[OH-].O1CCC[CH2:38]1.[C:42]([O:46]C)(=[O:45])[CH:43]=[CH2:44]>CO>[C:42]([OH:46])(=[O:45])[CH2:43][CH3:44].[CH3:38][N:8]1[C:4]2[CH:3]=[C:2]([Cl:1])[CH:35]=[CH:34][C:5]=2[N:6]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH:19]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)[CH2:12][CH2:11]2)[C:7]1=[O:9]

Participants

6

Reactant 4

HCID 961HydroxideHCID 7294Methyl AcrylateHCID 8028Tetrahydrofuran2×HCID 65449Clopimozide

Product 1

HCID 68139461HCID 68139461, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred mixture of 8.8 parts of 5-chloro-1-{1-[4,4-bis(p-fluorophenyl)butyl]-4-piperidyl}-2-benzimidazolinone, 1 part of N,N,N-trimethylbenzenemethanaminimum hydroxide solution 40% in methanol and 135 parts of tetrahydrofuran is added dropwise a solution of 8.6 parts of methyl 2-propenoate in 45 parts of tetrahydrofuran at 45° C. Upon completion, stirring is continued overnight at 50° C. The reaction mixture is evaporated. Water is added to the residue and the product is extracted with methylbenzene. The extract is dried, filtered and evaporated. The oily 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 oily residue is crystallized from a mixture of 2,2'-oxybispropane and 2-propanol, yielding methyl 6-chloro-3-{1-[4,4-bis(4-fluorophenyl)butyl]-4-piperidinyl}-1,3-dihydro-2-oxo-2H-benzimidazole 1-propanoate; mp. 186.2° C.

Workup

  1. customThe reaction mixture is evaporated
  2. additionWater is added to the residue
  3. extractionthe product is extracted with methylbenzene
  4. customThe extract is dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe oily residue is purified by column-chromatography over silicagel
  8. additiona mixture of trichloromethane and 5% of methanol as eluent
  9. customThe pure fractions are collected
  10. customthe eluent is evaporated
  11. customThe oily residue is crystallized from a mixture of 2,2'-oxybispropane and 2-propanol

Sources & evidence

ORD record
ord-90ae81e5d2784c35a27461e4a30657dc
Source dataset
uspto-grants-1976_11
Patent number
US03989707

Reaction notes

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