Methyl vinyl ketone → HCID 13769775, compound

HRID 979920Notes

Reaction equation

HRID 979920 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. (179).

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-a4c59bbc1a2748d9a4dfcbaf74c30f3f
Source dataset
uspto-grants-1987_01
Patent number
US04634704

Reaction notes

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