Bupropion → Bupropion toluene

HRID 1988312Notes

Reaction equation

HRID 1988312 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-70def4c5b03942288a9888aab942ce96
Source dataset
uspto-grants-2009_06
Patent number
US07553992B2

Reaction notes

Loading…