O-Phenylenediamine → N-[1-(1,2,2a,3,4,5-hexahydroacenaphthylen-1-yl)piperidin-4-yl]-benzene-1,2-diamine

HRID 331227Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 331227
[CH:1]1([N:13]2[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][CH:3]3[CH2:2]1.[C:20]1([NH2:27])[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[NH2:26].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>ClC(Cl)C.O.C(O)(=O)C>[CH:1]1([N:13]2[CH2:18][CH2:17][CH:16]([NH:26][C:21]3[C:20]([NH2:27])=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:15][CH2:14]2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][CH:3]3[CH2:2]1

Komponenten

8

Edukt 4

HCID 7243O-PhenylenediamineHCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 687066711-(1,2,2a,3,4,5-Hexahydroacenaphthylen-1-yl)piperidin-4-one

Produkt 1

HCID 68704972N-[1-(1,2,2a,3,4,5-hexahydroacenaphthylen-1-yl)piperidin-4-yl]-benzene-1,2-diamineAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

To a cooled (0° C.) solution of 1-(1,2,2a,3,4,5-hexahydroacenaphthylen-1-yl)piperidin-4-one (1.00 g, 3.92 mmol) and 1,2-phenylenediamine (642 mg) in dichloroethane (30 ml) were added sodium triacetoxyborohydride (1.99 g) and acetic acid (0.509 ml), and the mixture was stirred at room temperature for 19 hr. The reaction mixture was poured into water, and the mixture was neutralized with potassium carbonate, and extracted with chloroform. The extract was washed with water and saturated brine, dried over sodium sulfate, and concentrated. The obtained residue was purified by silica gel column chromatography (chloroform/methanol) to give N-[1-(1,2,2a,3,4,5-hexahydroacenaphthylen-1-yl)piperidin-4-yl]-benzene-1,2-diamine (1.16 g) as an oil.

Aufarbeitung

  1. extractionextracted with chloroform
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-c4558bebad384ff8a7c6d7786f699d6c
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877779B2

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