O-Methyltyramine → N-(2-p-methoxyphenylethyl)-p-fluorophenylpropionamide

HRID 1071985

Reaktionsgleichung

Reaktionsgleichung von HRID 1071985
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][CH2:8][NH2:9])=[CH:5][CH:4]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([CH3:23])[C:20](O)=[O:21])=[CH:15][CH:14]=1.Cl.CN(C)CCCN=C=NCC>ClCCl>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][CH2:8][NH:9][C:20](=[O:21])[CH:19]([C:16]2[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=2)[CH3:23])=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 4657O-MethyltyramineHCID 27239152-(4-Fluorophenyl)propionic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 86595127N-(2-p-methoxyphenylethyl)-p-fluorophenylpropionamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred mixture of p-methoxyphenethyl amine (3.28 g, 21.7 mmol), p-fluorophenyl propionic acid (3.31 g, 19.7 mmol), and 150 ml anhydrous dichloromethane was added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (4.16 g, 21.7 mmol). The mixture was stirred at ambient temperature for 40 hours and then washed with 1N sodium hydroxide, 1N hydrochloric acid, and saturated sodium chloride, dried, filtered and evaporated to a green solid (5.41 g, 91%). 1H NMR (CDCl3) δ 7.18 (m, 2H); 6.98 (m, 4 H); 6.81 (d, 2 H); 5.32 (br s, 1 H); 3.79 (s, 3 H); 3.44 (q, 2 H); 2.90 (t, 2 H); 2.68 (t, 2 H); 2.39 (t, 2 H).

Aufarbeitung

  1. washwashed with 1N sodium hydroxide, 1N hydrochloric acid, and saturated sodium chloride
  2. customdried
  3. filtrationfiltered
  4. customevaporated to a green solid (5.41 g, 91%)

Quellen und Nachweise

ORD-Eintrag
ord-82a3d6481c9940d29cbe58b48fd548d2
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06908931B2

Verknüpfte Notizen

Wird geladen…