Hydrogen Bromide → HCID 14518065, compound

HRID 2309647Notes

Reaction equation

HRID 2309647 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-038e2701f2ba4f9aaec9b337e0bcfda8
Source dataset
uspto-grants-1987_09
Patent number
US04695575

Reaction notes

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