Potassium Carbonate → N-(2-tert-butoxybenzyl)-3-(4-phenylpiperidin-1-yl)-N-(pyridin-2-ylmethyl)propan-1-amine

HRID 403126Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 403126
[C:1]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13]([O:17][C:18]1[CH:36]=[CH:35][CH:34]=[CH:33][C:19]=1[CH2:20][N:21]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1)[CH2:22][CH2:23][CH2:24]Cl)([CH3:16])([CH3:15])[CH3:14].C([O-])([O-])=O.[K+].[K+]>CC#N>[C:13]([O:17][C:18]1[CH:36]=[CH:35][CH:34]=[CH:33][C:19]=1[CH2:20][N:21]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1)[CH2:22][CH2:23][CH2:24][N:10]1[CH2:9][CH2:8][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12][CH2:11]1)([CH3:14])([CH3:15])[CH3:16]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 698734-PhenylpiperidineHCID 67128530N-(2-tert-butoxybenzyl)-3-chloro-N-(pyridin-2-ylmethyl)propan-1-amine

Produkt 1

HCID 70896369N-(2-tert-butoxybenzyl)-3-(4-phenylpiperidin-1-yl)-N-(pyridin-2-ylmethyl)propan-1-amineAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

4-phenyl piperidin (0.21 g, 1.2 mmol), compound 19 (0.3 g, 0.86 mmol), KI (0.43 g, 2.59 mmol) and K2CO3 (0.59 g, 4.3 mmol) were added to 50 mL CH3CN, and the solution was refluxed under argon atmosphere for 12 h. After cooling to room temperature, the inorganic salts were filtered, and the filtrate was evaporated to dryness. The residue was redissolved in CH2Cl2 and chromatographed on a silica gel TLC plate that was developed with the following eluents: 5% methanolic NH3 (7 M NH3 in methanol/95% CH2Cl2. The product was isolated as yellow oil (36% yield). 1H NMR (CDCl3) δ 8.492 (dd, 1H, Ar), 7.619 (ddd, 1H, Ar), 7.571 (t, 2H, Ar), 7.272 (t, 2H, Ar), 7.203 (d, 2H, Ar), 7.167 (t, 1H, Ar), 7.107 (m, 2H, Ar), 7.024 (t, 2H, Ar), 3.770 (s, 2H, —CH2—), 3.695, (s, 2H, —CH2—), 3.003 (d, 2H, —CH2—), 2.524 (t, 2H, —CH2—), 2.459 (m, 1H, —CH—), 2.367 (t, 2H, —CH2—), 2.01 (ddd, 2H, —CH2—), 1.783 (m, 6H), 1.359 (s, 9H, —C(CH3)3). Mass Spec.=472.34 (M+H)+.

Aufarbeitung

  1. temperaturethe solution was refluxed under argon atmosphere for 12 h
  2. filtrationthe inorganic salts were filtered
  3. customthe filtrate was evaporated to dryness
  4. dissolutionThe residue was redissolved in CH2Cl2
  5. customchromatographed on a silica gel TLC plate that

Quellen und Nachweise

ORD-Eintrag
ord-65184d20557141c19de14d68d5c22d18
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08747810B2

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