Sodium Carbonate → Bupropion

HRID 243571

Reaktionsgleichung

Reaktionsgleichung von HRID 243571
[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].Cl.C(=O)([O-])[O-].[Na+].[Na+]>O>[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]

Komponenten

4

Edukt 2

HCID 10340Sodium CarbonateHCID 62884Bupropion Hydrochloride

Produkt 1

HCID 444BupropionAusbeute 910,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

1.0 g of bupropion hydrochloride salt was dissolved in the minimum amount of water in 250 ml flask. The contents of the flask were transferred to a separatory funnel, to which 20 ml of 10% aqueous sodium carbonate was added, and the mixture was extracted with methylene chloride (3×50 ml). The combined methylene chloride extracts were washed with water (3×50 ml), then brine solution (50 ml), dried over anhydrous K2CO3, filtered and the filtrate stripped down under reduced pressure on a rotary evaporator to give the desired product as a yellow oil (7.9 g, 90% yield). 1H NMR (CDCl3, 400 MHz): δ 7.90 (s, 1H), 7.81 (d, j=7.8 Hz, 1H), 7.48 (d, j=7.8 Hz, 1H), 7.37 (dd, j1=j2=7.8 Hz, 1H), 4.24 (qt, J=7.2 Hz, 1H), 1.19 (d, j=7.2 Hz, 3H), 0.97 (s, 9H) ppm. ppm; MS m/z 240 (M+). LC-MS m/z 240 (M+) single peak at Rt=8.40 min.

Aufarbeitung

  1. additionwas added
  2. extractionthe mixture was extracted with methylene chloride (3×50 ml)
  3. washThe combined methylene chloride extracts were washed with water (3×50 ml)
  4. dry with materialbrine solution (50 ml), dried over anhydrous K2CO3
  5. filtrationfiltered
  6. customthe filtrate stripped down under reduced pressure on a rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-1084c52b361d49a995c461e86b173649
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653271B2

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