Acetaldehyde → HCID 19418793, Verbindung

HRID 864385Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 864385
C([BH3-])#N.[Na+].[CH3:5][C:6]([CH3:24])([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[NH2:23])[CH2:13][CH2:12]1)=[O:10])[CH3:7].[CH:25](=O)[CH3:26]>CO>[CH3:7][C:6]([CH3:24])([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[NH:23][CH2:25][CH3:26])[CH2:13][CH2:12]1)=[O:10])[CH3:5]

Komponenten

5

Edukt 3

HCID 177AcetaldehydeHCID 2795530tert-Butyl 4-(2-aminophenyl)piperazine-1-carboxylateHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 19418793HCID 19418793, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Sodium cyanoborohydride (1.6 g) is added to a 0° solution of 1-[1,1-dimethylethoxycarbonyl]-4-(2-aminophenyl)piperazine (PREPARATION 13, 6.52 g) and acetaldehyde (1.48 ml) dissolved in methanol (65 ml). After 3 hr the reaction mixture is partially concentrated under reduced pressure. Then it is diluted with chloroform, washed with saturated aqueous sodium bicarbonate, saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound, Rf =0.62 (ethyl acetate/hexane, 1/1), NMR (300 MHz, CDCl3) 7.04, 6.95, 6.66, 4.59, 3.70-3.50, 3.15, 2.82, 1.49 and 1.28δ.

Aufarbeitung

  1. concentrationAfter 3 hr the reaction mixture is partially concentrated under reduced pressure
  2. additionThen it is diluted with chloroform
  3. washwashed with saturated aqueous sodium bicarbonate, saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7719c1a027f44af8982725764d0bfbe9
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05563142

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