Cyclopropylamine → 4-Bromo-2-cyclopropylaminomethyl-benzoic acid isopropyl ester

HRID 1869960Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1869960
[CH:1]([O:4][C:5](=[O:15])[C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:7]=1[CH2:13]Br)([CH3:3])[CH3:2].[CH:16]1([NH2:19])[CH2:18][CH2:17]1>C(#N)C>[CH:1]([O:4][C:5](=[O:15])[C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:7]=1[CH2:13][NH:19][CH:16]1[CH2:18][CH2:17]1)([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 69828CyclopropylamineHCID 574242524-Bromo-2-bromomethyl-benzoic acid isopropyl ester2×

Produkt 1

HCID 574242534-Bromo-2-cyclopropylaminomethyl-benzoic acid isopropyl esterAusbeute 28,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A stirred, cooled (ice bath) solution of 4-bromo-2-bromomethyl-benzoic acid isopropyl ester (Intermediate 118, 5.1 g, 15.17 mmol) in acetonitrile (25 mL) was treated with cyclopropyl amine (2 mL, 28.9 mmol). The reaction mixture was allowed to warm to ambient temperature. After 2 h, the volatiles were evaporated in vacuo, the residue was diluted with water and extracted with diethyl ether (×2). The combined organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to an oil. Flash column chromatography over silica gel (230-400 mesh) using 4-20% ethyl acetate in hexane as the eluent to afforded the title product (1.33 g, 28%).

Aufarbeitung

  1. customthe volatiles were evaporated in vacuo
  2. additionthe residue was diluted with water
  3. extractionextracted with diethyl ether (×2)
  4. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo to an oil

Quellen und Nachweise

ORD-Eintrag
ord-72dda06c916141a2a04170fa20a9ac9d
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638648B2

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