Methanol → N-[4-(4-aminophenoxy)-2-pyridinyl]-4-(1-pyrrolidinylmethyl)-1-piperidinecarboxamide

HRID 492961Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 492961
[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][CH:21]([CH2:24][N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)[CH2:20][CH2:19]3)=[O:17])[CH:10]=2)=[CH:6][CH:5]=1)([O-])=O.CO>O1CCCC1.[C].[Pd]>[NH2:1][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[CH2:19][CH2:20][CH:21]([CH2:24][N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)[CH2:22][CH2:23]3)=[O:17])[CH:10]=2)=[CH:6][CH:5]=1

Komponenten

5

Edukt 2

HCID 887MethanolHCID 86602175N-[4-(4-Nitrophenoxy)-2-pyridinyl]-4-(1-pyrrolidinylmethyl)-1-piperidinecarboxamide

Produkt 1

HCID 59596970N-[4-(4-aminophenoxy)-2-pyridinyl]-4-(1-pyrrolidinylmethyl)-1-piperidinecarboxamideAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-(Pyrrolidin-1-ylmethyl)piperidine-1-carboxylic acid [4-(4-nitrophenoxy)pyridin-2-yl]amide (295 mg) was dissolved in tetrahydrofuran (7 ml) and methanol (7 ml) under a nitrogen atmosphere, and then 10% palladium carbon (147 mg) was added, followed by stirring under a hydrogen atmosphere for 10 hrs. The reaction mixture was filtered to remove the catalyst, and the catalyst was washed with methanol. The filtrate was concentrated to give a residue, which was then purified by silica gel column chromatography (Fuji Silysia NH, eluent; ethyl acetate). Fractions containing a target compound were concentrated to provide 4-(pyrrolidin-1-ylmethyl)piperidine-1-carboxylic acid [4-(4-aminophenoxy)pyridin-2-yl]amide (233.7 mg) as white foam.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-fcb15444790e4e3fba5fc75b987440df
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531532B2

Notizen zur Reaktion

Wird geladen…