Diisopropylethylamine → 3-chloro-N-(2-morpholin-4-ylethyl)-4-nitro-benzamide

HRID 2234371Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2234371
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5](Cl)=[O:6].C(N(CC)C(C)C)(C)C.[NH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([NH:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)=[O:6]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 4082852-MorpholinoethylamineHCID 190776143-Chloro-4-nitrobenzoyl chloride2×

Produkt 1

HCID 686820563-chloro-N-(2-morpholin-4-ylethyl)-4-nitro-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

3-chloro-4-nitro-benzoyl chloride (Intermediate 54; 1.1 g, 5.00 mmol) was dissolved in DCM (10 mL) and N,N-diisopropylethylamine (1.05 mL, 6.00 mmol) added. The mixture was cooled in an ice/water bath and 4-(2-aminoethyl)morpholine (Aldrich; 0.66 mL, 5.00 mmol) in DCM (5 mL) added dropwise. The mixture was allowed to warm to room temperature and stirred for 0.5 hr. The reaction mixture was washed with brine, 2N NaOH, dried (MgSO4) and concentrated. Column chromatography of the residue (2% MeoH/DCM) gave the title compound as a yellow solid. (1.2 g, 76%)

Aufarbeitung

  1. temperatureThe mixture was cooled in an ice/water bath
  2. washThe reaction mixture was washed with brine, 2N NaOH
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3f315437d9a14764a797a75efcb37da4
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709471B2

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