Dimethyl Sulfoxide → HCID 23345200, compound

HRID 1856567Notes

Reaction equation

HRID 1856567 reaction equation
[CH3:1][N:2]([CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:14][CH2:13]1)[C:3]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[N:4]=1.CS(C)=O.[H-].[Na+].[Cl:32][CH2:33][C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1>C1C=CC=CC=1>[ClH:32].[ClH:32].[F:40][C:37]1[CH:38]=[CH:39][C:34]([CH2:33][N:7]2[C:6]3[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=3[N:4]=[C:3]2[N:2]([CH3:1])[CH:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:14][CH2:13]2)=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 96024-Fluorobenzyl chlorideHCID 24758Sodium hydrideHCID 12891517HCID 12891517, compound

Product 1

HCID 23345200HCID 23345200, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred and cooled (below 5° C.) mixture of 3.3 parts of N-methyl-N-[1-(2-phenylethyl)-4-piperidinyl]-1H-benzimidazol-2-amine, 100 parts of dimethylsulfoxide and 90 parts of benzene are added 0.5 parts of sodium hydride dispersion 50%. After stirring for 30 minutes, 1.5 parts of 1-(chloromethyl)-4-fluorobenzene are added and stirring is continued overnight while the mixture is allowed to reach room temperature. The reaction mixture is poured onto water and the product is extracted with methylbenzene. The extract is dried, filtered and evaporated. The residue is converted into the hydrochloride salt in 2-propanone. The salt is filtered off and crystallized from 2-propanol, yielding 2.8 parts (54.4%) of 1-[(4-fluorophenyl)methyl]-N-methyl-N-[1-(2-phenylethyl)-4-piperidinyl]-1H-benzimidazol-2-amine dihydrochloride; mp. 246.6° C.

Workup

  1. temperaturecooled
  2. stirringAfter stirring for 30 minutes
  3. stirringstirring
  4. customto reach room temperature
  5. additionThe reaction mixture is poured onto water
  6. extractionthe product is extracted with methylbenzene
  7. customThe extract is dried
  8. filtrationfiltered
  9. customevaporated
  10. filtrationThe salt is filtered off
  11. customcrystallized from 2-propanol

Sources & evidence

ORD record
ord-544a4b6c43694ae487e92925dde5d3af
Source dataset
uspto-grants-1980_08
Patent number
US04219559

Reaction notes

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