Dimethyl Sulfoxide → 2-Methyl-11-[(S)-3-phenethyl-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepine

HRID 1350515Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1350515
Cl.[CH3:2][C:3]1[CH:18]=[CH:17][C:6]2[NH:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[N:10]=[C:11]([NH2:12])[C:5]=2[CH:4]=1.[CH2:19]([C@H:27]1[CH2:32]N[CH2:30][CH2:29][NH:28]1)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)C(C)C)(C)C.CS(C)=O>C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH3:2][C:3]1[CH:18]=[CH:17][C:6]2[NH:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[N:10]=[C:11]([N:12]3[CH2:30][CH2:29][NH:28][C@@H:27]([CH2:19][CH2:20][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:32]3)[C:5]=2[CH:4]=1

Komponenten

7

Edukt 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 210935072-Methyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochlorideHCID 44828673(S)-2-Phenethylpiperazine

Produkt 1

HCID 588606152-Methyl-11-[(S)-3-phenethyl-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepineAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Combine 2-methyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochloride (600.0 mg, 2.31 mmol), (S)-2-phenethyl-piperazine (879.1 mg, 4.62 mmol), N,N-diisopropylethylamine (298.6 mg, 2.31 mmol), DMSO (1.0 ml), and toluene (4.0 ml). Stir and heat the mixture at 110° C. After 67 hours, cool the mixture to ambient temperature and then dilute it with ethyl acetate. Wash the organic layer with 0.1 N NaOH and brine. Dry (sodium sulfate) and concentrate the organic layer to residue. Purify the residue on silica gel using dichloromethane/methanol (90:10) to give 646.3 mg (71%) of a tan foam: mp 67°, dec; mass spectrum (ion spray): m/z=397.3 (M+1).

Aufarbeitung

  1. temperaturecool the mixture to ambient temperature
  2. washWash the organic layer with 0.1 N NaOH and brine
  3. dry with materialDry (sodium sulfate)
  4. concentrationconcentrate the organic layer to residue
  5. customPurify the residue on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-2288989fe3d94ee5b3740f1572a636ee
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07214673B2

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