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Ammonium formate → (5-Amino-2-(4-methylpiperazin-1-yl)phenyl)methanol

HRID 1190870
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1190870
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][C:9]=2[CH2:17][OH:18])[CH2:4][CH2:3]1.C([O-])=O.[NH4+]>CCO.[Pd]>[NH2:14][C:11]1[CH:12]=[CH:13][C:8]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[C:9]([CH2:17][OH:18])[CH:10]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 25918812[2-(4-Methylpiperazino)-5-nitrophenyl]methanol

Produkt 1

HCID 36995517(5-Amino-2-(4-methylpiperazin-1-yl)phenyl)methanolAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

[2-(4-Methylpiperazin-1-yl)-5-nitrophenyl]methanol prepared in step A of example 1 (1.00 g, 3.98 mmol) was hydrogenated using ammonium formate (2.51 g, 10 eq) and Pd/C (10% Pd, 0.43 mg, 0.1 eq) in 50 mL of EtOH. The mixture was stirred overnight at room temperature and then filtered through a celite pad. The filtrate was evaporated and the residue was dissolved in DCM and washed with an saturated aqueous solution of Na2CO3. The aqueous layer was extracted with DCM. The combined organic layers were dried over Na2SO4, filtered and evaporated to yield expected compound as a pale yellow oil (0.85 g, 97% yield).

Aufarbeitung

  1. filtrationfiltered through a celite pad
  2. customThe filtrate was evaporated
  3. dissolutionthe residue was dissolved in DCM
  4. washwashed with an saturated aqueous solution of Na2CO3
  5. extractionThe aqueous layer was extracted with DCM
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-9c2f6784ad24477b9389ca1675cf4541
Quelldatensatz
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08680095B2

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