Benzoyl chloride → HCID 14277502, Verbindung

HRID 1461749Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1461749
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C@H:11]1[CH2:25][C@H:24]2[C@@H:14]([CH2:15][C:16]3[C:26]4[C:19](=[CH:20][CH:21]=[CH:22][C:23]2=4)[NH:18][CH:17]=3)[N:13]([CH2:27][CH2:28][CH3:29])[CH2:12]1>C(Cl)Cl.C(N(CC)CC)C>[C:1]([NH:10][C@H:11]1[CH2:25][C@H:24]2[C@@H:14]([CH2:15][C:16]3[C:26]4[C:19](=[CH:20][CH:21]=[CH:22][C:23]2=4)[NH:18][CH:17]=3)[N:13]([CH2:27][CH2:28][CH3:29])[CH2:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 7412Benzoyl chlorideHCID 134688038alpha-Amino-6-n-propylergoline

Produkt 1

HCID 14277502HCID 14277502, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

1.4 ml benzoylchloride in 5 ml CH2Cl2 are added drop-wise with stirring at 5°-10° C. to a suspension of 3.0 g 8α-amino-6-n-propylergoline in 100 ml CH2Cl2 and 2.0 ml triethylamine. The obtained reaction mixture is stirred for 15 to 20 hours at 20° C. and then washed thoroughly 2× with 25 ml 2N NaOH and H2O. The organic phase is dried over MgSO4, filtered and evaporated. The residue (pale brown foam) is dissolved in ethanol, and crystallised as the hydrobromide by addition of equivalent amounts of HBr in acetic acid. M.P. on recrystallisation from C2H5OH/H2O (80:2)=290° with decomposition.

Aufarbeitung

  1. customThe obtained reaction mixture
  2. washwashed thoroughly 2× with 25 ml 2N NaOH and H2O
  3. dry with materialThe organic phase is dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionThe residue (pale brown foam) is dissolved in ethanol
  7. customcrystallised as the hydrobromide by addition of equivalent amounts of HBr in acetic acid
  8. customM.P. on recrystallisation from C2H5OH/H2O (80:2)=290° with decomposition

Quellen und Nachweise

ORD-Eintrag
ord-9012bb01317a4757b0e5e9c0ea6ce225
Quelldatensatz
uspto-grants-1991_12
Patentnummer
US05077298

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