Cyclohexanemethylamine → N-cyclohexylmethyl-3-[4-(3,3-diphenyl-1-propyl)piperazin-1-yl]benzamide

HRID 1796741Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1796741
[C:1]1([CH:7]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=3)[C:19](O)=[O:20])[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[CH:67]1([CH2:73][NH2:74])[CH2:72][CH2:71][CH2:70][CH2:69][CH2:68]1>ClCCl>[CH:67]1([CH2:73][NH:74][C:19](=[O:20])[C:18]2[CH:22]=[CH:23][CH:24]=[C:16]([N:13]3[CH2:12][CH2:11][N:10]([CH2:9][CH2:8][CH:7]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH2:15][CH2:14]3)[CH:17]=2)[CH2:72][CH2:71][CH2:70][CH2:69][CH2:68]1

Komponenten

6

Edukt 4

HCID 76688CyclohexanemethylamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 221804873-[4-(3,3-Diphenyl-1-propyl)piperazin-1-yl]benzoic acid

Produkt 1

HCID 22180288N-cyclohexylmethyl-3-[4-(3,3-diphenyl-1-propyl)piperazin-1-yl]benzamideAusbeute 91,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The compound (0.12 g) prepared in step (c) of Example 1 was dissolved in dichloromethane (5 ml), and a BOP reagent (0.16 g) and diisopropylethylamine (0.078 ml) were added to the solution. The mixture was stirred at room temperature for 30 min. Cyclohexanemethylamine (0.057 ml) was then added thereto, and the mixture was stirred at room temperature overnight. The reaction solution was extracted with ethyl acetate, followed by washing with water. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was then removed by distillation under the reduced pressure. The residue was purified by preparative TLC (hexane:ethyl acetate=1:1) to give 0.13 g (91.6%) of N-cyclohexylmethyl-3-[4-(3,3-diphenyl-1-propyl)piperazin-1-yl]benzamide.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionThe reaction solution was extracted with ethyl acetate
  3. washby washing with water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was then removed by distillation under the reduced pressure
  6. customThe residue was purified by preparative TLC (hexane:ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-de07585438e0438185015c4e67ce7ae2
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07030120B2

Notizen zur Reaktion

Wird geladen…