Hydrogen Bromide → Bupropion Hydrobromide

HRID 1911710Notes

Reaction equation

HRID 1911710 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

Conditions

Temperature
80 °C

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° C. to 40° C. 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 (80° C.), to get complete solution of the suspended solid. The temperature was then lowered to 25° C. in 1 hour and further lowered to 0-5° C. 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 50° C. 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° C. to 40° C
  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. customto get complete solution of the suspended solid
  9. customfurther lowered to 0-5° C. in 1 additional hour
  10. customThe precipitate obtained
  11. filtrationwas filtered
  12. washwashed with 20 ml of cold isopropanol
  13. customThe discharged wet solid was dried under vacuum (30 mmHg) in a static drier at 50° C. for 16 hours

Sources & evidence

ORD record
ord-e0bb31ffa0f44b4697ed3e13dec868be
Source dataset
uspto-grants-2013_12
Patent number
US08604085B2

Reaction notes

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