Hydrogen Bromide → HCID 14518065, compound

HRID 1904849Notes

Reaction equation

HRID 1904849 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[CH2:18][CH:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][C:27](=[O:29])[CH3:28])[CH2:21][CH2:20]2)=[CH:4][CH:3]=1.[BrH:30].BrBr>C(O)(=O)C>[BrH:30].[BrH:30].[BrH:30].[Br:30][CH2:28][C:27](=[O:29])[CH2:26][CH2:25][N:22]1[CH2:21][CH2:20][CH:19]([CH2:18][C:10]2[N:9]([CH2:8][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=2)[CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24408BromineHCID 14012902HCID 14012902, compound

Product 1

HCID 14518065HCID 14518065, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

A mixture of 85 parts of 4-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]methyl]-1-piperidinyl]-2-butanone and 600 parts of acetic acid was acidified with glacial acetic acid saturated with hydrogen bromide. A solution of 32.6 parts of bromine in acetic acid was added dropwise. Upon completion, stirring was continued overnight at room temperature. The reaction mixture was evaporated. The residue was stirred in 4-methyl-2-pentanone. The product was filtered off and dried, yielding 111 parts (80%) of 1-bromo-4-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]methyl]-1-piperidinyl]-2-butanone trihydrobromide (458).

Workup

  1. customThe reaction mixture was evaporated
  2. stirringThe residue was stirred in 4-methyl-2-pentanone
  3. filtrationThe product was filtered off
  4. customdried

Sources & evidence

ORD record
ord-6fe86875aa154868be23714a1967cd4e
Source dataset
uspto-grants-1989_06
Patent number
US04839374

Reaction notes

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