Water → Tert-butyl 4-(6-bromopyridin-3-yl)-1,4-diazepane-1-carboxylate

HRID 2182270

Reaktionsgleichung

Reaktionsgleichung von HRID 2182270
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9][CH2:8]2)[CH:2]=1.[Br:21]N1C(=O)CCC1=O.O>C(#N)C>[Br:21][C:6]1[N:1]=[CH:2][C:3]([N:7]2[CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9][CH2:8]2)=[CH:4][CH:5]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 108024941-(Pyridin-3-yl)-4-tert-butoxycarbonylhomopiperazine

Produkt 1

HCID 22478562Tert-butyl 4-(6-bromopyridin-3-yl)-1,4-diazepane-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1-(3-Pyridyl)-4-tert-butoxycarbonyl homopiperazine (25.0 g, 90.1 mmol) was solved in acetonitrile (400 ml) and cooled to 0° C. N-Bromosuccinimide (19.3 g, 108.2 mmol) was added during 10 min. Water (400 ml) was added and the mixture was extracted twice with diethyl ether (200 ml). Chromatography on silica gel with a mixture of petroleum: ethyl acetate (1:1) gave the title compound as free base. Yield 18.7 g, 58%.

Aufarbeitung

  1. extractionthe mixture was extracted twice with diethyl ether (200 ml)
  2. additionChromatography on silica gel with a mixture of petroleum: ethyl acetate (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-ef958457bc004d1daadb6440c6752247
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06897219B2

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