1,2-Diphenylethylamine → N-cyano-N'-(1,2-diphenylethyl)-3-pyridinecarboximidamide

HRID 1588540

Reaktionsgleichung

Reaktionsgleichung von HRID 1588540
[C:1]([N:3]=[C:4]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)OC(C)C)#[N:2].[C:15]1([CH:21]([NH2:29])[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CO>[C:1]([NH:3][C:4]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)=[N:29][CH:21]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)#[N:2]

Komponenten

4

Edukt 2

HCID 264821,2-DiphenylethylamineHCID 100812013-Pyridinecarboximidic acid, N-cyano-, 1-methylethyl ester

Produkt 1

HCID 19734548N-cyano-N'-(1,2-diphenylethyl)-3-pyridinecarboximidamideAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Isopropyl N-cyano-3-pyridinecarboximidate (0.60 g, 3.2 mmol) was dissolved in methanol (10 ml), and 1,2-diphenylethylamine (0.69 g, 3.5 mmol) was added. The mixture was stirred at room temperature for 45 minutes. After the reaction was completed, the reaction solution was concentrated under reduced pressure. The residual concentrate thus obtained was subjected to chromatography on a silica gel column (WAKO GEL C-200, 50 g) eluting with chloroform-methanol (100:1). The eluted fractions were concentrated under reduced pressure to give N-cyano-N'-(1,2-diphenylethyl)-3-pyridinecarboximidamide (0.60 g, 1.8 mmol, yield: 58%) as colorless syrup. Next, to this syrup was added a 5% hydrogen chloride solution in methanol (2.5 ml). The solution was crystallized from methanol-diethyl ether to give N-cyano-N'-(1,2-diphenylethyl)-3-pyridinecarboximidamide hydrochloride as colorless powder.

Aufarbeitung

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. concentrationThe residual concentrate thus
  3. customobtained
  4. washeluting with chloroform-methanol (100:1)
  5. concentrationThe eluted fractions were concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f2c1281b52de4a81925814674fea22ff
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05223508

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