Triethylamine → 2-Dimethylamino-1-(7-methoxy-8-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-ethanone

HRID 1041247Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1041247
[CH3:1][O:2][C:3]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11][C:5]=2[CH:4]=1.Cl.[CH3:18][N:19]([CH2:21][C:22](Cl)=[O:23])[CH3:20].C(N(CC)CC)C>ClCCl>[CH3:18][N:19]([CH3:20])[CH2:21][C:22]([N:9]1[CH2:10][CH2:11][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:6]=2[CH2:7][CH2:8]1)=[O:23]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 139949912-(Dimethylamino)acetyl chloride hydrochlorideHCID 672643517-Methoxy-8-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Produkt 1

HCID 672643662-Dimethylamino-1-(7-methoxy-8-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Into a 1-neck round-bottom flask was added 7-methoxy-8-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.490 g, 2.20 mmol), dimethylamino-acetyl chloride hydrochloride (0.4181 g, 2.646 mmol), and Triethylamine (0.7683 mL, 5.512 mmol) in dichloromethane (11 mL) and the reaction was stirred overnight at room temperature. The reaction mixture was next partitioned between water and ethyl acetate, and the layers separated. The aqueous phase was extracted twice with EtOAc and the combined organic extract was washed with water, dried (MgSO4), filtered, and concentrated, and the product, 2-dimethylamino-1-(7-methoxy-8-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-ethanone, was isolated by flash chromatography (SiO2, MeOH/dichloromethane 0-10%) as an oil (600 mg, 90%). LC/MS (ESI+): 308.04 (M+H).

Aufarbeitung

  1. customThe reaction mixture was next partitioned between water and ethyl acetate
  2. customthe layers separated
  3. extractionThe aqueous phase was extracted twice with EtOAc
  4. extractionthe combined organic extract
  5. washwas washed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-403889dd265c466daf7b65e4e1e4a61b
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552186B2

Notizen zur Reaktion

Wird geladen…