Carbon Dioxide → (4-Amino-3-{[3-(cyclohexyl-methyl-amino)-propylamino]-methyl}-phenyl)-phenyl-methanone

HRID 390245Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 390245
[C:1]([C:9]1[CH:10]=[CH:11][C:12]([N+:17]([O-])=O)=[C:13]([CH:16]=1)[CH:14]=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S1[CH:24]=[CH:23][CH:22]=[CH:21]1.[CH3:25][NH:26][CH2:27][CH2:28][CH2:29][NH2:30].C(=O)=O.[CH2:34]1COC[CH2:35]1>[Pd]>[NH2:17][C:12]1[CH:11]=[CH:10][C:9]([C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:8])=[CH:16][C:13]=1[CH2:14][NH:30][CH2:29][CH2:28][CH2:27][N:26]([CH:21]1[CH2:35][CH2:34][CH2:24][CH2:23][CH2:22]1)[CH3:25]

Komponenten

7

Edukt 5

HCID 280Carbon DioxideHCID 8028TetrahydrofuranHCID 8030ThiopheneHCID 80511N-Methyl-1,3-propanediamineHCID 198160555-Benzoyl-2-nitrobenzaldehyde

Produkt 1

HCID 58625047(4-Amino-3-{[3-(cyclohexyl-methyl-amino)-propylamino]-methyl}-phenyl)-phenyl-methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

A mixture of 5-benzoyl-2-nitrobenzaldehyde (0.0058 mol) in THF (100 ml) was hydrogenated with 10% Pd/C (1 g) as a catalyst in the presence of 4% thiophene solution (1 mL). After uptake of H2 (3 equiv), the mixture was put in an autoclave. N-cyclohexyl, N-methyl-propane-1,3-diamine (0.01 mol) and CaH2 (0.5 g) were added and the mixture was reacted under 10 atm of CO2 and 50 atm of H2 at 50° C. for 16 hours. When the reaction was complete, the mixture was purified over silica gel on a glass filter (eluent: 90:10 CH2Cl2:(CH3OH:NH3)). The product fractions were collected and the solvent was evaporated to yield the title compound as a residue.

Aufarbeitung

  1. customthe mixture was purified over silica gel on a glass
  2. filtrationfilter (eluent: 90:10 CH2Cl2:(CH3OH:NH3))
  3. customThe product fractions were collected
  4. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-b90822cd5d1d45dea07d384512c8d672
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383637B2

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