Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-(4-Fluorobenzoyl)piperidine | HCID 2724440 | — |
| Reactant | 5-chloro-1,3-dihydro-2-oxo-2H-benzimidazole-1-propanol methanesulfonate | HCID 21424816 | — |
| Solvent | Methyl Isobutyl Ketone | HCID 7909 | — |
| Product | Milenperone | HCID 65489 | 10% |
Reaction Steps
A mixture of 5.5 parts of 3-(5-chloro-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl methanesulfonate, 3.6 parts of (4-fluorophenyl) (4-piperidinyl) methanone, 6 parts of sodium carbonate and 80 parts of 4-methyl-2-pentanone is stirred and refluxed overnight. After cooling, the reaction mixtue is filtered and the filtrate is evaporated. The residue is purified by column-chromatography over silica gel 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 4-methyl-2-pentanone. The product is filtered off and recrystallized from 4-methyl-2-pentanone, yielding 0.6 parts (10%) of 5-chloro-1-{3-[4-(4-fluorobenzoyl)-1-piperidinyl] propyl} -1,3-dihydro-2H-benzimidazol-2-one; mp. 163.7° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US04035369 |
|---|
| Source dataset | uspto-grants-1977_07 |
|---|
| ORD ID | ord-4cc7d476fa38487f8e40dec50a64eece |
|---|
| Source note | uspto-grants-1977_07 |
|---|