Hydrogen Bromide → HCID 20145262, compound

HRID 648638Notes

Reaction equation

HRID 648638 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:7]=[CH:8][C:9]([N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[C:10]([CH:12]([CH:14]([C:24]([NH2:26])=[O:25])[C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=2)[CH3:13])[CH:11]=1.[OH-].[Na+].[BrH:35]>O.[Cu]Br>[Br:35][C:6]1[CH:7]=[CH:8][C:9]([N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[C:10]([CH:12]([CH:14]([C:24]([NH2:26])=[O:25])[C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=2)[CH3:13])[CH:11]=1

Participants

7

Reactant 4

HCID 260Hydrogen Bromide2×HCID 14798Sodium HydroxideHCID 20145241HCID 20145241, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 20145262HCID 20145262, compound

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 962WaterSolvent

Procedure

A solution of 0.072 gm (1.05 m mol) of sodium nitrite in 0.5 ml of water was added dropwise at an internal temperature of 0° to 5° C. to 0.40 gm (1.05 m mol) of 4-[(1-(5-amino-2-piperidino-phenyl)-ethyl)-aminocarbonylmethyl]-benzoic acid in 2 ml of semi-concentrated aqueous hydrobromic acid. The thus obtained diazonium salt solution was then added dropwise to 0.196 gm of copper-(I) bromide in 2 ml of 48% hydrobromic acid, whereby strong formation of gas occurred. The reaction mixture was stirred for 1.5 hours at an internal temperature of 45° to 50° C., cooled, and adjusted to pH 4 by means of 4N sodium hydroxide solution. After extraction with warm ethyl acetate, the extract was washed with water, dried, and filtered. After evaporation in vacuo, the residue obtained was purified by column chromatography on silica gel (chloroform/methanol=7:1).

Workup

  1. temperaturecooled
  2. extractionAfter extraction with warm ethyl acetate
  3. washthe extract was washed with water
  4. customdried
  5. filtrationfiltered
  6. customAfter evaporation in vacuo
  7. customthe residue obtained
  8. customwas purified by column chromatography on silica gel (chloroform/methanol=7:1)

Sources & evidence

ORD record
ord-35d78875dcd5464793779c4b5b06333b
Source dataset
uspto-grants-1988_04
Patent number
US04735959

Reaction notes

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