Phenacyl bromide → HCID 13769713, compound

HRID 979945Notes

Reaction equation

HRID 979945 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[NH:18][CH:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][NH:27][C:28]([NH2:30])=[S:29])[CH2:21][CH2:20]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:38][C:39]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=O>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[NH:18][CH:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][NH:27][C:28]3[S:29][CH:38]=[C:39]([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[N:30]=3)[CH2:21][CH2:20]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 13769777HCID 13769777, compound

Product 1

HCID 13769713HCID 13769713, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred mixture of 4.3 parts of N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]thiourea, 2.1 parts of potassium carbonate and 40 parts of methanol was added dropwise a solution of 2 parts of 2-bromo-1-phenylethanone in methanol. Upon completion, stirring was continued for overnight at room temperature. The reaction mixture was filtered over Hyflo and the filtrate was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile, yielding 2.5 parts of 1-[(4-fluorophenyl)methyl]-N-[1-[2-[(4-phenyl-2-thiazolyl)amino]ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine; mp. 176.2° C. (compound 89).

Workup

  1. filtrationThe reaction mixture was filtered over Hyflo
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated
  7. customThe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-81d48cea79484af498d729f3988af510
Source dataset
uspto-grants-1987_01
Patent number
US04634704

Reaction notes

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