4-[2-(Azetidin-1-yl)ethyl]piperazine-1-carboxylic acid [4-(4-nitrophenoxy)pyridin-2-yl]amide → 4-[2-(Azetidin-1-yl)ethyl]piperazine-1-carboxylic acid [4-(4-aminophenoxy)pyridin-2-yl]amide

HRID 492993Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 492993
[N+:1]([C:4]1[CH:31]=[CH:30][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]3[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][N:26]4[CH2:29][CH2:28][CH2:27]4)[CH2:20][CH2:19]3)=[O:17])[CH:10]=2)=[CH:6][CH:5]=1)([O-])=O>O1CCCC1.CO.[C].[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]3[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][N:26]4[CH2:29][CH2:28][CH2:27]4)[CH2:20][CH2:19]3)=[O:17])[CH:10]=2)=[CH:30][CH:31]=1

Komponenten

5

Edukt 1

HCID 576776864-[2-(Azetidin-1-yl)ethyl]piperazine-1-carboxylic acid [4-(4-nitrophenoxy)pyridin-2-yl]amide

Produkt 1

HCID 576775264-[2-(Azetidin-1-yl)ethyl]piperazine-1-carboxylic acid [4-(4-aminophenoxy)pyridin-2-yl]amideAusbeute 61,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-[2-(Azetidin-1-yl)ethyl]piperazine-1-carboxylic acid [4-(4-nitrophenoxy)pyridin-2-yl]amide (122 mg) was dissolved in tetrahydrofuran (3 ml) and methanol (3 ml). 10% Palladium carbon (61 mg) was added, followed by stirring under a hydrogen atmosphere for 22 hrs. The reaction mixture was filtered to remove the catalyst, and the catalyst was washed with methanol. The filtrate was concentrated under reduced pressure to give a residue, which was then purified by silica gel column chromatography (Fuji Silysia NH, eluent; ethyl acetate:methanol=9:1). Fractions containing the target compound were concentrated to give a crude product of the titled compound (70 mg) as a pale yellow oil.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. washthe catalyst was washed with methanol
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto give a residue, which
  6. customwas then purified by silica gel column chromatography (Fuji Silysia NH, eluent; ethyl acetate:methanol=9:1)
  7. additionFractions containing the target compound
  8. concentrationwere concentrated

Quellen und Nachweise

ORD-Eintrag
ord-9206415103584da38e5e506488c8a256
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531532B2

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