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

HRID 1153741Notes

Reaction equation

HRID 1153741 reaction equation
S(=O)(=O)=O.[BrH:5].Br.[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][N:13]=1.Br>FC(Cl)(F)C(Cl)(Cl)F.ClCCl>[Br:5][C:15]1[CH:16]=[C:17]([CH3:18])[C:12]([CH2:11][CH2:10][CH2:9][CH2:8][NH2:7])=[N:13][CH:14]=1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 24682Sulfur trioxideHCID 23325013HCID 23325013, compound

Product 1

HCID 130942724-(5-Bromo-3-methyl-2-pyridinyl)butylamineYield 51.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6428Cfc 113Solvent2×

Procedure

A solution of sulphur trioxide (150 ml) in 1,1,2-tri-fluorotrichloroethane (350 ml) was added over ca 30 min. to a suspension of 2-(4-aminobutyl)-3-methyl-pyridine dihydrobromide (17 g) [prepared by passing hydrogen bromide gas through a solution of the amine in dichloromethane] in 1,1,2-trifluorotrichloroethane (100 ml) and 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-aminobutyl)-3-methylpyridine (6.53 g) as an oil.

Workup

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

Sources & evidence

ORD record
ord-3e6338cd8f9c4f3394cd5888f8c1df58
Source dataset
uspto-grants-1984_12
Patent number
US04486434

Reaction notes

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