3-Phenylpropylamine → 5-Hydroxypyridine-2-carboxylic acid (3-phenylpropyl)amide

HRID 389973

Reaktionsgleichung

Reaktionsgleichung von HRID 389973
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.C(N(C(C)C)CC)(C)C.O.ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.Cl.[C:43]1([CH2:49][CH2:50][CH2:51][NH2:52])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>ClCCl>[C:43]1([CH2:49][CH2:50][CH2:51][NH:52][C:8]([C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][N:6]=2)=[O:10])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Komponenten

7

Edukt 5

HCID 162593-PhenylpropylamineHCID 81531DiisopropylethylamineHCID 2687405-Hydroxypyridine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Produkt 1

HCID 860284705-Hydroxypyridine-2-carboxylic acid (3-phenylpropyl)amideAusbeute 61,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 5-hydroxypyridine-2-carboxylic acid (0.103 g, 0.74 mmol) in dichloromethane was added diisopropylethylamine (0.279 mL, 1.6 mmol), followed by 1-hydroxybenzotriazole monohydrate (0.012 g, 0.8 mmol) and EDCl (0.153 g, 0.8 mmol). The resulting mixture was stirred for 15 minutes and 3-phenyl-1-propylamine (0.108 g, 0.8 mmol) was added. After stirring for 22 h, the reaction mixture was diluted with dichloromethane (80 mL), washed with water, dried over anhydrous Na2SO4 and concentrated in vacuo. Purification by column chromatography afforded 5-hydroxypyridine-2-carboxylic acid (3-phenylpropyl)amide as white crystals (0.116 g, 61% yield). MS (ES+) m/z 257.2 (M+1).

Aufarbeitung

  1. stirringAfter stirring for 22 h
  2. washwashed with water
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a9fa6b3d185c4673b13359a4b947e175
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383628B2

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