Potassium Carbonate → (R)-N-[1-(4-Pyrrolidinophenethyl)pyrrolidin-3-yl]-2-(2-bromobenzyloxy)aniline

HRID 2251914Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2251914
CS(O[C@H:6]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:15][CH:14]=2)[CH2:7]1)(=O)=O.[Br:24][C:25]1[CH:39]=[CH:38][CH:37]=[CH:36][C:26]=1[CH2:27][O:28][C:29]1[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=1[NH2:31].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N:19]1([C:16]2[CH:17]=[CH:18][C:13]([CH2:12][CH2:11][N:8]3[CH2:9][CH2:10][C@@H:6]([NH:31][C:30]4[CH:32]=[CH:33][CH:34]=[CH:35][C:29]=4[O:28][CH2:27][C:26]4[CH:36]=[CH:37][CH:38]=[CH:39][C:25]=4[Br:24])[CH2:7]3)=[CH:14][CH:15]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 112081902-(o-Bromobenzyloxy) anilineHCID 59643988(S)-3-methanesulfonyloxy-1-(4-pyrrolidinophenethyl)pyrrolidine

Produkt 1

HCID 69200293(R)-N-[1-(4-Pyrrolidinophenethyl)pyrrolidin-3-yl]-2-(2-bromobenzyloxy)aniline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

(S)-3-Methanesulfonyloxy-1-(4-pyrrolidinophenethyl)pyrrolidine (0.30 g, 0.89 mmol) was added to 2-(2-bromobenzyloxy)aniline (1.15 g, 4.13 mmol) in argon stream. The obtained mixture was dissolved in acetonitrile (50 ml). Potassium carbonate (1.62 g, 11.7 mmol) was added to the obtained solution, and they were refluxed for 85 hours. Acetonitrile (15 ml) was added to the reaction mixture, and they were refluxed for additional 48 hours. The reaction mixture was filtered through Celite to obtain the filtrate. The solvent was evaporated under reduced pressure to obtain the title compound in the form of a brown oily mixture (1.40 g).

Aufarbeitung

  1. temperaturewere refluxed for 85 hours
  2. temperaturewere refluxed for additional 48 hours
  3. filtrationThe reaction mixture was filtered through Celite
  4. customto obtain the filtrate
  5. customThe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c502d0469d1446b08c33f2fa20d0e565
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07320973B2

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