Fumaric Acid → N-(2-Methylpropyl)-N-[(quinolin-3-yl)methyl]piperidin-4-amine fumarate

HRID 2111892Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2111892
[CH3:1][CH:2]([CH3:22])[CH2:3][N:4]([CH2:11][C:12]1[CH:13]=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27]>C(OCC)C.CO>[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27].[CH3:1][CH:2]([CH3:22])[CH2:3][N:4]([CH2:11][C:12]1[CH:13]=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:5]1[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]1

Komponenten

5

Edukt 2

HCID 444972Fumaric AcidHCID 57640314N-(2-methylpropyl)-N-[(quinolin-3-yl)methyl]piperidin-4-amine

Produkt 1

HCID 68574554N-(2-Methylpropyl)-N-[(quinolin-3-yl)methyl]piperidin-4-amine fumarateAusbeute 76,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

N-(2-Methylpropyl)-N-[(quinolin-3-yl)methyl]piperidin-4-amine (0.74 g, 2.50 mmol) is dissolved in diethyl ether (35 ml) and methanol (6 ml). Fumaric acid (0.29 g, 2.50 mmol), in warm methanol (4 ml), is then added. Diethyl ether (100 ml) is added and the solution is heated. The solution is slowly cooled and then placed in the freezer. The solid is filtered and washed with diethyl ether to yield (0.79 g, 76%) of the title product: mass spectrum (ion spray): m/z=298.1 (M+1); 1H NMR (DMSO-d6): δ=8.84 (d, 1H), 8.16 (d, 1H), 7.98-7.91 (m, 2H), 7.71-7.68 (m, 1H), 7.58-7.54 (m, 1H), 6.42 (s, 2H), 3.75 (s, 2H), 3.25-3.22 (m, 2H), 2.76-2.70 (m, 3H), 2.21 (d, 2H), 1.83-1.59 (m, 6H), 0.76 (d, 6H).

Aufarbeitung

  1. temperaturethe solution is heated
  2. temperatureThe solution is slowly cooled
  3. filtrationThe solid is filtered
  4. washwashed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-aecd0983cc464ee784cff57d8d0a4ce1
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07521462B2

Notizen zur Reaktion

Wird geladen…