Putrescine → 4,5,6,7-tetrahydro-2[2-(4-pyridyl)ethyl]-1H-1,3-diazepine

HRID 364718

Reaktionsgleichung

Reaktionsgleichung von HRID 364718
[C:1]([CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1)#[N:2].[NH2:11][CH2:12][CH2:13][CH2:14][CH2:15]N.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.NCCCCN.CC[O-].[Na+]>C(O)C>[N:8]1[CH:9]=[CH:10][C:5]([CH2:4][CH2:3][C:1]2[NH:11][CH2:12][CH2:13][CH2:14][CH2:15][N:2]=2)=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 1045PutrescineHCID 2723922Sodium ethoxideHCID 73304614-PyridinepropanenitrileHCID 202397711,4-Diaminobutane di-p-toluenesulfonate

Produkt 1

HCID 132811944,5,6,7-tetrahydro-2[2-(4-pyridyl)ethyl]-1H-1,3-diazepineAusbeute 93,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

The mixture of 4-[2-cyanoethyl]pyridine (1.32 g, 0.01M), 1,4-diaminobutane (0.88 g, 0.01M) and 1,4-diaminobutane di-p-toluenesulfonate (4.32 g, 0.01M) was heated at about 190° to about 200° C. for 4 hrs. The residue was stirred with ethanol (20 ml) which contained EtONa (0.02M) and filtered. The filtrate was concentrated and distilled at 0.07 mmHg and a temperature of about 180° to about 200° C. to give 4,5,6,7-tetrahydro-2[2-(4-pyridyl)ethyl]-1H-1,3-diazepine (1.9 g, 93% yield).

Aufarbeitung

  1. temperaturewas heated at about 190° to about 200° C. for 4 hrs
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. distillationdistilled at 0.07 mmHg

Quellen und Nachweise

ORD-Eintrag
ord-b0e070306c3c4a50b63785f89189f544
Quelldatensatz
uspto-grants-1986_08
Patentnummer
US04605744

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