Bromine → 4-(5-Bromo-3-methyl-2-pyridinyl)butylamine

HRID 1381016Notes

Reaction equation

HRID 1381016 reaction equation
S(=O)(=O)=O.[BrH:5].[NH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][N:12]=1.BrBr>FC(Cl)(F)C(Cl)(Cl)F>[Br:5][C:14]1[CH:15]=[C:16]([CH3:17])[C:11]([CH2:10][CH2:9][CH2:8][CH2:7][NH2:6])=[N:12][CH:13]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 24682Sulfur trioxideHCID 23325010HCID 23325010, compound

Product 1

HCID 130942724-(5-Bromo-3-methyl-2-pyridinyl)butylamineYield 46.1%

Reagents, catalysts & solvents 1

HCID 6428Cfc 113Solvent2×

Procedure

A solution of sulphur trioxide (150 ml) in 1,1,2-tri-fluorotrichloroethane (550 ml) was added over 30 min to a suspension of 2-(4-aminobutyl)-3-methyl-pyridine hydrobromide (14.2 g) [prepared by reacting 2-(4-aminobutyl)-3-methyl-pyridine with hydrobromic acid (0.89M)] in 1,1,2-trifluoro-trichloroethane and to this mixture was added liquid bromine (5.56 g). The mixture was heated under reflux for ca 16 hr. The solvent was removed by distillation and unbrominated starting material was removed by acetylation as described in Example 1(h) to yield 5-bromo-2-(4-amino-butyl)-3-methylpyridine (6.49 g) as an oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for ca 16 hr
  3. customThe solvent was removed by distillation
  4. customwas removed by acetylation

Sources & evidence

ORD record
ord-007d43d7f90a4b6c8d66fc003d39e8c4
Source dataset
uspto-grants-1986_04
Patent number
US04584381

Reaction notes

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