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Tert-Butylamine → Bupropion

HRID 17017
Notes
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Reaction equation

HRID 17017 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[Cl:6][C:7]1[CH:8]=[C:9]([C:13](=[O:17])[CH:14](Br)[CH3:15])[CH:10]=[CH:11][CH:12]=1>>[CH3:15][CH:14]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C:13]([C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([Cl:6])[CH:8]=1)=[O:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 6385Tert-ButylamineHCID 4992116alpha-Bromo-3-chloropropiophenone

Product 1

HCID 444Bupropion

Procedure

t-Butylamine was added to m-chloro-α-bromopropiophenone obtained above and the reaction mixture was refluxed for 3 hours. Excessive t-butylamine was removed by evaporation below 80° C. The concentrated solution was cooled down to room temperature and then extracted with 800 ml of ethyl acetate and 280 ml of water. The organic phase was dried with anhydrous magnesium sulfate (15 g) to obtain a solution of bupropion free base. A solution of HCl in ethyl acetate was added at room temperature to the organic phase. Crude product of bupropion hydrochloride was obtained after filtration. The crude product of bupropion hydrochloride was dissolved in 1200 ml of methanol and 120 ml of water at 80° C., decolorized with activated carbon (5 g) for 20 minutes and filtered. The filtrate was cooled and filtered to obtain wet product of bupropion hydrochloride. The wet product was dried in vacuum (−0.04˜−0.09 MPa, 80° C.) for 3 hours to obtain pure product. Total yield was 70% based on m-chloropropiophenone, and the HPLC's purify was higher than or equal to 99.9%.

Workup

  1. customobtained above and the reaction mixture
  2. temperaturewas refluxed for 3 hours
  3. customExcessive t-butylamine was removed by evaporation below 80° C
  4. extractionextracted with 800 ml of ethyl acetate and 280 ml of water
  5. dry with materialThe organic phase was dried with anhydrous magnesium sulfate (15 g)

Sources & evidence

ORD record
ord-44aba63233bb40459fa6f8f8b08df596
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07737302B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes