Benzoyl chloride → HCID 18919752, Verbindung

HRID 1291168Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1291168
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1(C)C=CC=CC=1>[C:25]([O:15][CH:12]1[CH2:11][CH2:10][N:9]([CH2:8][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:17][CH:16]=2)[CH2:14][CH2:13]1)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

5

Edukt 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 765041HCID 765041, Verbindung

Produkt 1

HCID 18919752HCID 18919752, VerbindungAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

0.3 g (0.00127mol) of 1-(4-nitro-benzyl)-piperidin-4-ol and 0.356 ml (0.00254 mol) of triethylamine were dissolved in 10 ml of toluene, treated with 0.177 ml (0.0015 mol) of benzoyl chloride and boiled at reflux for 18 hrs. The reaction mixture was concentrated and the residue was chromatographed over silica gel with ethyl acetate/hexane (1:2). 0.335 g (78%) of 1-(4-nitro-benzyl)-piperidin-4-yl benzoate was obtained as yellow crystals. MS: me/e (% basic peak)=340 (C19H20O4+, 3.5), 235 (5), 218 (41), 105 (26), 82 (100).

Aufarbeitung

  1. temperatureat reflux for 18 hrs
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was chromatographed over silica gel with ethyl acetate/hexane (1:2)

Quellen und Nachweise

ORD-Eintrag
ord-2acf412163854f46baa96262a751e875
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05753679

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