5-Nitrofurfural → 5-(Nitro-furan-2-ylmethyl)-(2-piperidin-1-yl-phenyl)-amine

HRID 33467

Reaktionsgleichung

Reaktionsgleichung von HRID 33467
[N:1]1([C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[NH2:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:14]([C:17]1OC(C=O)=[CH:19][CH:18]=1)([O-:16])=[O:15].C(O[BH-](O[C:34](=[O:36])[CH3:35])OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[N+:14]([CH:17]([C:18]1[O:36][CH:34]=[CH:35][CH:19]=1)[C:11]1[CH:12]=[CH:13][C:7]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[C:8]([NH2:9])[CH:10]=1)([O-:16])=[O:15]

Komponenten

5

Edukt 3

HCID 127745-NitrofurfuralHCID 4587952-(Piperidin-1-yl)anilineHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 865957225-(Nitro-furan-2-ylmethyl)-(2-piperidin-1-yl-phenyl)-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 2-piperidinoaniline (1 mmol), 5-nitro-furan-2-carbaldehyde (1.1 mmol) and sodium triacetoxyborohydride (“NaBH(OAc)3”) (2 mmol) in anhydrous DCM (10 mL) was stirred 16 h at room temperature. The mixture was then washed successively with water, dilute aqueous sodium hydroxide (“NaOH”), water and brine before being dried over MgSO4, filtered and concentrated under reduced pressure. Purification of the residual oil by flash silica gel chromatography yielded the product. MS: 301 (M+1). LC/MS purity: 100%. 1H NMR (CDCl3, 300 MHz): δ 7.25 (d, 1H), 7.15-6.95 (m, 2H), 6.75 (t, 1H), 6.55 (d, 1H), 5.4 (bs, 1H), 4.45 (s, 2H), 2.8 (bm, 4H), 1.8-1.5 (bm, 6H).

Aufarbeitung

  1. washThe mixture was then washed successively with water, dilute aqueous sodium hydroxide (“NaOH”), water and brine
  2. dry with materialbefore being dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residual oil by flash silica gel chromatography
  6. customyielded the product

Quellen und Nachweise

ORD-Eintrag
ord-f1581ed5899248c99cc9d8b5f38f94e0
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429603B2

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