O-Methyltyramine → 1-(4-chlorophenyl)-N-[2-(4-methoxyphenyl)ethyl]cyclopropanecarboxamide

HRID 1850873

Reaktionsgleichung

Reaktionsgleichung von HRID 1850873
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([OH:13])=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][NH2:24])=[CH:18][CH:17]=1.Cl.C(N=C=NCCCN(C)C)C>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:11]([NH:24][CH2:23][CH2:22][C:19]3[CH:20]=[CH:21][C:16]([O:15][CH3:14])=[CH:17][CH:18]=3)=[O:13])[CH2:9][CH2:10]2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 4657O-MethyltyramineHCID 986061-(p-Chlorophenyl)cyclopropanecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 604096681-(4-chlorophenyl)-N-[2-(4-methoxyphenyl)ethyl]cyclopropanecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 1-(4-chlorophenyl)cyclopropanecarboxylic acid (5.0 g, 25.3 mmol), 2-(4-methoxyphenyl)ethanamine (4.2 g, 28 mmol) and 4-N,N-Dimethylaminopyridin (3.3 g; 28 mmol) in methylenehloride (200 ml) was cooled to −10° C. N-ethyl-N′-(3-Dimethylaminopropyl)-carbodiimid hydrochloride (EDC, 5.3 g, 28 mmol) was added in several portions and the resulting mixture stirred overnight. The reaction mixture was poured into water and consecutively extracted with water, 2N NaOH and 1N HCl. Evaporation of the dried (NaSO4) extract yielded an oily residue that crystallized upon addition of n-heptan, which was used without further purification. Yield 7.0 g (21.2 mmol, 83%).

Aufarbeitung

  1. extractionconsecutively extracted with water, 2N NaOH and 1N HCl
  2. customEvaporation of the
  3. dry with materialdried (NaSO4)
  4. extractionextract
  5. customyielded an oily residue that
  6. customcrystallized upon addition of n-heptan, which
  7. customwas used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-bef0d4a902b649ad986996cdb96c4d6a
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957089B2

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