Triethylamine → 4-[[2-[(Diethylamino)methyl]-1-piperidinyl]acetyl]-1,3-dimethyl-1,4,9,10-tetrahydropyrrolo[3,2-b][1,5]benzodiazepin-10-one

HRID 465068

Reaktionsgleichung

Reaktionsgleichung von HRID 465068
Cl[CH2:2][C:3]([N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[NH:9][C:8](=[O:16])[C:7]2[N:17]([CH3:21])[CH:18]=[C:19]([CH3:20])[C:6]1=2)=[O:4].C(N(CC)CC)C.[CH2:29]([N:31]([CH2:34][CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][NH:36]1)[CH2:32][CH3:33])[CH3:30]>CN(C)C=O>[CH2:29]([N:31]([CH2:34][CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][N:36]1[CH2:2][C:3]([N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[NH:9][C:8](=[O:16])[C:7]2[N:17]([CH3:21])[CH:18]=[C:19]([CH3:20])[C:6]1=2)=[O:4])[CH2:32][CH3:33])[CH3:30]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 254287N,N-Diethyl-2-piperidinemethanamineHCID 202615044-Chloroacetyl-1,3-dimethyl-1,4,9,10-tetrahydropyrrolo[3,2-b][1,5]benzodiazepin-10-one

Produkt 1

HCID 135785884-[[2-[(Diethylamino)methyl]-1-piperidinyl]acetyl]-1,3-dimethyl-1,4,9,10-tetrahydropyrrolo[3,2-b][1,5]benzodiazepin-10-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4-(chloroacetyl)-1,3-dimethyl-1,4,9,10-tetrahydropyrrolo[3,2-b][1,5]-benzodiazepin-10-one (2.0 g, 0.0066 mol), dimethylformamide (30 ml), triethylamine (1 ml, 0.0071 mol) and 2-[(diethylamino)methyl]piperidine (1.7 g, 0.01 mol) is heated to 30°-40° C. for two hours with stirring. The solvent is distilled off under water jet vacuum, the residue taken up in water (10 ml), made alkline with potassium carbonate and extracted exhaustively with dichloromethane. The combined methylene chloride extracts are dried over sodium sulfate and concentrated. The crude product thus obtained is purified by chromatography on silica gel using dichloromethane/methanol (9:1 v/v). After recrystallization from ethyl acetate/methanol (95:5) the desired compound (1.4 g) is obtained in the form of colorless crystals, Mp. 176°-178° C.

Aufarbeitung

  1. temperatureis heated to 30°-40° C. for two hours
  2. distillationThe solvent is distilled off under water jet vacuum
  3. extractionextracted exhaustively with dichloromethane
  4. dry with materialThe combined methylene chloride extracts are dried over sodium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-657633666d054e6b84af060207e1a96d
Quelldatensatz
uspto-grants-1985_10
Patentnummer
US04550107

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