Bupropion → Bupropion toluene

HRID 1363421Notes

Reaction equation

HRID 1363421 reaction equation
ClCC[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.BrBr.C(N)(C)(C)C.[CH3:19][CH:20]([NH:30][C:31]([CH3:34])([CH3:33])[CH3:32])[C:21]([C:23]1[CH:24]=[CH:25][CH:26]=[C:27]([Cl:29])[CH:28]=1)=[O:22]>C(Cl)Cl>[CH3:19][CH:20]([NH:30][C:31]([CH3:32])([CH3:34])[CH3:33])[C:21]([C:23]1[CH:24]=[CH:25][CH:26]=[C:27]([Cl:29])[CH:28]=1)=[O:22].[C:6]1([CH3:4])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 444BupropionHCID 6385Tert-ButylamineHCID 24408BromineHCID 702953-Chloropropiophenone

Product 1

HCID 66960545Bupropion toluene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloro-propiophenone starting material was brominated in methylene chloride by dropping bromine under controlled conditions. On reaction completion the mother liquor was worked up and then the second reaction was executed by transferring the bromoderivative solution onto the tert-butylamine. The second substitution reaction (the tert-butylamine amino-group substitutes the bromine atom) forms the final bupropion molecule. After work up of the mother liquor, a bupropion toluene solution was obtained. The solvent was evaporated and bupropion was dissolved in isopropanol. From the isopropanol solution, the hydrobromide was precipitated with hydrogen bromide gas. On precipitation completion, the product was centrifuged, washed with isopropanol and dried under vacuum. On dryer discharge approval it was discharged in Kraft drums within double polyethylene bags.

Workup

  1. customOn reaction completion the mother liquor
  2. customthe second reaction

Sources & evidence

ORD record
ord-744fa42e6a5f493baaaf32257a40cc26
Source dataset
uspto-grants-2011_02
Patent number
US07884136B2

Reaction notes

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