Diisopropylethylamine → 4-(5-Fluoro-4-methyl-2-nitro-phenylamino)piperidine-1-carboxylic acid tert-butyl ester

HRID 1716605

Reaktionsgleichung

Reaktionsgleichung von HRID 1716605
Cl[C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH3:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([NH2:26])[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].CCN(C(C)C)C(C)C>C(Cl)Cl>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([NH:26][C:2]2[CH:7]=[C:6]([F:8])[C:5]([CH3:9])=[CH:4][C:3]=2[N+:10]([O-:12])=[O:11])[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 875934-Chloro-2-fluoro-5-nitrotolueneHCID 12682914-Amino-1-Boc-piperidine

Produkt 1

HCID 588522794-(5-Fluoro-4-methyl-2-nitro-phenylamino)piperidine-1-carboxylic acid tert-butyl esterAusbeute 18,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

A mixture of 1-chloro-5-fluoro-4-methyl-2-nitro-benzene (2 g, 10.55 mmol), 4-amino-piperidine-1-carboxylic acid tert-butyl ester (2.32 g, 11.58 mmol), and iPr2NEt (3.8 mL) was heated for 2 hours at 180° C. by microwave heating. After cooling, the reaction mixture was diluted with CH2Cl2 and then filtered. The volatiles were removed under reduced pressure and the residue was purified by flash chromatography (25% ethyl acetate in hexanes) to afford 4-(5-fluoro-4-methyl-2-nitro-phenylamino)piperidine-1-carboxylic acid tert-butyl ester (0.68 g, 18%) as a brown solid.

Aufarbeitung

  1. temperatureheating
  2. temperatureAfter cooling
  3. filtrationfiltered
  4. customThe volatiles were removed under reduced pressure
  5. customthe residue was purified by flash chromatography (25% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-2baa627bd70b408b9964623461bffd6c
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803816B2

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