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

HRID 462500Notes

Reaction equation

HRID 462500 reaction equation
S(=O)(=O)=O.[BrH:5].Br.[CH3:7][C:8]1[C:9]([CH2:14][CH2:15][CH2:16][CH2:17][NH2:18])=[N:10][CH:11]=[CH:12][CH:13]=1.Br>FC(Cl)(F)C(Cl)(Cl)F.ClCCl>[Br:5][C:12]1[CH:13]=[C:8]([CH3:7])[C:9]([CH2:14][CH2:15][CH2:16][CH2:17][NH2:18])=[N:10][CH:11]=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-trifluorotrichloroethane (350 ml) was added over ca 30 min. to a suspension of 4-(3-methyl-2-pyridyl)butylamine 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(b) to yield 4-(5-bromo-3-methyl-2-pyridyl)-butylamine (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-145153409f4d4cddaf72f583e286a52d
Source dataset
uspto-grants-1985_05
Patent number
US04515952

Reaction notes

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