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

HRID 1381015Notes

Reaction equation

HRID 1381015 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-methylpyridine 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-amino-butyl)-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-03b406396cc4407da174583ef48c54d9
Source dataset
uspto-grants-1986_04
Patent number
US04584381

Reaction notes

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