Hydrogen Bromide → HCID 20222896, compound

HRID 979921Notes

Reaction equation

HRID 979921 reaction equation
[BrH:1].Br.[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]=[C:12]2[NH:20][CH:21]2[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][C:29](=[O:32])[CH2:30][CH3:31])[CH2:23][CH2:22]2)=[CH:6][CH:5]=1.Br.BrBr>C(O)(=O)C>[BrH:1].[BrH:1].[Br:1][CH:30]([CH3:31])[C:29](=[O:32])[CH2:28][CH2:27][N:24]1[CH2:25][CH2:26][CH:21]([NH:20][C:12]2[N:11]([CH2:10][C:7]3[CH:8]=[CH:9][C:4]([F:3])=[CH:5][CH:6]=3)[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]=2)[CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24408BromineHCID 20222930HCID 20222930, compound

Product 1

HCID 20222896HCID 20222896, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a stirred mixture of 37.5 parts of 1-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]-3-pentanone dihydrobromide and 500 parts of acetic acid was added a hydrobromic acid solution in glacial acetic acid. Then there were added slowly dropwise 10.5 parts of bromine. Upon completion, stirring was continued overnight at room temperature. The reaction mixture was evaporated and the residue was suspended in 2-propanone. The product was filtered off and dried, yielding 37.5 parts (89%) of 4-bromo-1-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]-3-pentanone dihydrobromide (183).

Workup

  1. customThe reaction mixture was evaporated
  2. filtrationThe product was filtered off
  3. customdried

Sources & evidence

ORD record
ord-f01d3962ec2c485db52bb86940baa45a
Source dataset
uspto-grants-1987_01
Patent number
US04634704

Reaction notes

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