Pyrrolidine → N-(2-amino-5-bromophenyl)pyrrolidine-1-carboxamide

HRID 62699Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 62699
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-])=O)=[C:6]([CH:8]=1)[NH2:7].ClC(Cl)(O[C:16](=[O:22])OC(Cl)(Cl)Cl)Cl.[NH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1>ClCCl>[NH2:9][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:8][C:6]=1[NH:7][C:16]([N:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:22]

Komponenten

5

Edukt 3

HCID 31268PyrrolidineHCID 94429TriphosgeneHCID 53147665-Bromo-2-nitroaniline

Produkt 1

HCID 86712537N-(2-amino-5-bromophenyl)pyrrolidine-1-carboxamideAusbeute 34,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 5-bromo-2-nitroaniline (1 g, 4.61 mmol) in dichloromethane (15 mL) were added TEA (8.35 mL, 59.9 mmol, 1.3 eq.) and triphosgene (1.37 g, 4.61 mmol, 1 equiv.) at 0° C. The mixture was stirred for three hours at room temperature and the pyrrolidine (0.39 g, 5.53 mmol, 1.2 equiv.) was added slowly. The reaction was stirred for an additional two hours. The reaction crude was diluted with dichloromethane and washed with water and brine. The organic layers were dried over MgSO4, filtered and evaporated. The residue was purified by column chromatography on eluting ethyl acetate and hexane to allow N-(2-amino-5-bromophenyl)pyrrolidine-1-carboxamide (0.45 g, 31% yield).

Aufarbeitung

  1. stirringThe reaction was stirred for an additional two hours
  2. customThe reaction crude
  3. washwashed with water and brine
  4. dry with materialThe organic layers were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography
  8. washon eluting ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-bc741af4a26c43ffb06e37aa6e257499
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447030B2

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