Methyl vinyl ketone → HCID 13769775, compound

HRID 1493905Notes

Reaction equation

HRID 1493905 reaction equation
[CH3:1][C:2](=[O:5])[CH:3]=[CH2:4].[F:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]=[C:15]2[NH:23][CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:9][CH:8]=1>C(O)C>[F:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]=[C:15]2[NH:23][CH:24]2[CH2:25][CH2:26][N:27]([CH2:4][CH2:3][C:2](=[O:5])[CH3:1])[CH2:28][CH2:29]2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 6570Methyl vinyl ketoneHCID 123618Tecastemizole

Product 1

HCID 13769775HCID 13769775, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.1 parts of 3-buten-2-one, 9.7 parts of 1-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-1H-benzimidazol-2-amine and 120 parts of ethanol was stirred for 3 hours at reflux temperature. The reaction mixture was evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of 2-propanone and 2,2'-oxybispropane, yielding 5 parts (42%) of 4-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]-2-butanone; mp. 131.3° C. (intermediate 91).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. customThe residue was purified by column-chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated
  7. customThe residue was crystallized from a mixture of 2-propanone and 2,2'-oxybispropane

Sources & evidence

ORD record
ord-921421b081b245838a6caa65cc1d7ebf
Source dataset
uspto-grants-1991_06
Patent number
US05025014

Reaction notes

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