Chloroacetone → 1-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]-2-propanone

HRID 845780Notes

Reaction equation

HRID 845780 reaction equation
Cl[CH2:2][C:3](=[O:5])[CH3:4].Br.Br.[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]=[C:17]2[NH:25][CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]=[C:17]2[NH:25][CH:26]2[CH2:27][CH2:28][N:29]([CH2:2][C:3](=[O:5])[CH3:4])[CH2:30][CH2:31]2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 10340Sodium CarbonateHCID 3018631Norastemizole hydrobromide

Product 1

HCID 135880761-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]-2-propanoneYield 39.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 9.25 parts of 1-chloro-2-propanone, 48.6 parts of 1-(4-fluorophenylmethyl)-N-(4-piperidinyl)-1H-benzimidazol-2-amine dihydrobromide, 32 parts of sodium carbonate and 135 parts of N,N-dimethylformamide was stirred and heated overnight at 50° C. The reaction mixture was poured onto water and the product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The residue was crystallized from 4-methyl-2-pentanone, yielding 15 parts (39.5%) of 1-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]-2-propanone (intermediate 130).

Workup

  1. additionThe reaction mixture was poured onto water
  2. extractionthe product was extracted with 4-methyl-2-pentanone
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was crystallized from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-2994ab3879f74ad8aacd885cf4893122
Source dataset
uspto-grants-1988_07
Patent number
US04760074

Reaction notes

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