Betahistine → HCID 779568, compound

HRID 1590127Notes

Reaction equation

HRID 1590127 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7]Cl)([O-:3])=[O:2].[CH3:12][NH:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1.C(N(CC)CC)C>CO>[CH3:12][N:13]([CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[CH2:7][C:6]1[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

5

Reactant 3

HCID 2366BetahistineHCID 8471TriethylamineHCID 12078alpha-Chloro-m-nitrotoluene

Product 1

HCID 779568HCID 779568, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Conditions

Temperature
40 °C

Procedure

6.8 g of 3-nitrobenzyl chloride in 25 ml of methanol are slowly added dropwise to a solution of 5.4 g of 2-(2-methylaminoethyl)pyridine in 20 ml of methanol at 40° C. 15 ml of triethylamine in 15 ml of methanol are subsequently added, and the mixture is stirred for 15 hours at 40° C. After removal of the solvent by evaporation in vacuo, the residue is taken up in 300 ml of water and extracted three times with dichloromethane. After drying over sodium sulphate, the dichloromethane is evaporated in vacuo and the residue is chromatographed on silica gel (eluent: dichloromethane/methanol 100:5).

Workup

  1. customAfter removal of the solvent
  2. customby evaporation in vacuo
  3. extractionextracted three times with dichloromethane
  4. dry with materialAfter drying over sodium sulphate
  5. customthe dichloromethane is evaporated in vacuo
  6. customthe residue is chromatographed on silica gel (eluent: dichloromethane/methanol 100:5)

Sources & evidence

ORD record
ord-f9c36a9a2099443ab3afc3d0f2e5135f
Source dataset
uspto-grants-1993_04
Patent number
US05202336

Reaction notes

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