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4-Pyridinemethanamine → 4-[2-(4-Aminomethylpiperidin-1-yl)ethyl]phenyl 9-acridinecarboxylate

HRID 565131
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 565131
[CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]=2[C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25]OS(C4C=CC(C)=CC=4)(=O)=O)=[CH:20][CH:19]=2)=[O:16])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[NH2:37][CH2:38][C:39]1[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=1.CC([O-])(C)C.[K+]>CN(C=O)C>[CH:11]1[C:12]2[C:7](=[N:6][C:5]3[C:14]([C:13]=2[C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][N:42]4[CH2:43][CH2:44][CH:39]([CH2:38][NH2:37])[CH2:40][CH2:41]4)=[CH:20][CH:19]=2)=[O:16])=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:8]=[CH:9][CH:10]=1
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Komponenten

5

Edukt 3

HCID 773174-PyridinemethanamineHCID 158957504-(2-Tosyloxyethyl)phenyl 9-acridine carboxylateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 158957514-[2-(4-Aminomethylpiperidin-1-yl)ethyl]phenyl 9-acridinecarboxylateAusbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228Dimethylformamide
Lösungsmittel

Versuchsvorschrift

In 30 ml of DMF, 2.9 g of the compound (3) obtained in Example 3 were dissolved, followed by the addition of 0.59 g of 4-aminomethylpyridine. The resultant mixture was stirred at room temperature, to which 0.60 g of t-BuOK was added under ice cooling. The thus-obtained mixture was stirred at room temperature for 5 hours. The DMF was distilled off under reduced pressure, and the residue was dissolved in CHCl3. The solution so obtained was washed with water and then dried over anhydrous magnesium sulfate (MgSO4). The solvent was distilled off under reduced pressure. The residue was isolated and purified by chromatography on a silica gel column (eluent: CHCl3/MeOH=7/3), whereby 0.41 g of the compound (4) was obtained (yield: 18%).

Aufarbeitung

  1. additionwas added under ice cooling
  2. distillationThe DMF was distilled off under reduced pressure
  3. dissolutionthe residue was dissolved in CHCl3
  4. customThe solution so obtained
  5. washwas washed with water
  6. dry with materialdried over anhydrous magnesium sulfate (MgSO4)
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThe residue was isolated
  9. custompurified by chromatography on a silica gel column (eluent: CHCl3/MeOH=7/3)

Quellen und Nachweise

ORD-Eintrag
ord-260f2e7543064e24a97e714f5a418534
Quelldatensatz
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06171520B2

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