Hydrogen Bromide → Bupropion Hydrobromide

HRID 1295210Notes

Reaction equation

HRID 1295210 reaction equation
[CH3:1][CH:2]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([Cl:11])[CH:10]=1)=[O:4].[BrH:17]>C(O)(C)C>[CH3:1][CH:2]([NH:12][C:13]([CH3:14])([CH3:16])[CH3:15])[C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([Cl:11])[CH:10]=1)=[O:4].[BrH:17]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 444Bupropion

Product 1

HCID 11984562Bupropion HydrobromideYield 74.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A 250 ml flask equipped with overhead stirrer and gas inlet was charged with 34 g of bupropion base and 138 ml of isopropanol. The solution was maintained under stirring while 13 g of gaseous HBr was introduced through the gas inlet in a time of 20′ while the internal temperature of the mixture raises from 25 to 40oC. During the gas addition a heavy white precipitate formed. At the end of the gas addition the temperature of the mixture was raised to reflux (80oC), to get complete solution of the suspended solid. The temperature was then lowered to 25oC in 1 hour and further lowered to 0-5oC in 1 additional hour. The precipitate obtained was filtered and washed with 20 ml of cold isopropanol. The discharged wet solid was dried under vacuum (30 mmHg) in a static drier at 50oC for 16 hours. 34 g of bupropion hydrobromide form I were obtained.

Workup

  1. customA 250 ml flask equipped with overhead stirrer and gas inlet
  2. temperatureThe solution was maintained
  3. temperatureraises from 25 to 40oC
  4. additionDuring the gas addition a heavy white precipitate
  5. customformed
  6. additionAt the end of the gas addition the temperature of the mixture
  7. temperaturewas raised
  8. temperatureto reflux (80oC)
  9. customto get complete solution of the suspended solid
  10. customfurther lowered to 0-5oC in 1 additional hour
  11. customThe precipitate obtained
  12. filtrationwas filtered
  13. washwashed with 20 ml of cold isopropanol
  14. customThe discharged wet solid was dried under vacuum (30 mmHg) in a static drier at 50oC for 16 hours

Sources & evidence

ORD record
ord-79e4b655d3294cc0ab5213e607c3dc84
Source dataset
uspto-grants-2007_07
Patent number
US07241805B2

Reaction notes

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