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Water → Ethyl trans-[(7-chloro-1,2,3,4,10,14b-hexahydro-10-methyldibenzo[b,f]pyrido[1,2-d][1,4]diazepin-1-yl)amino]acetate

HRID 16186
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 16186
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[N:6]([CH3:20])[C:7]3[CH:19]=[CH:18][CH:17]=[CH:16][C:8]=3[C@@H:9]3[C@H:14]([NH2:15])[CH2:13][CH2:12][CH2:11][N:10]3[C:4]=2[CH:3]=1.Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].C(N(CC)CC)C.O>CN(C=O)C>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[N:6]([CH3:20])[C:7]3[CH:19]=[CH:18][CH:17]=[CH:16][C:8]=3[C@@H:9]3[C@H:14]([NH:15][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:13][CH2:12][CH2:11][N:10]3[C:4]=2[CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 86599897trans-7-Chloro-1,2,3,4,10,14b-hexahydro-10-methyldibenzo[b,f]pyrido[1,2-d][1,4]-diazepin-1-ylamine

Produkt 1

HCID 86599896Ethyl trans-[(7-chloro-1,2,3,4,10,14b-hexahydro-10-methyldibenzo[b,f]pyrido[1,2-d][1,4]diazepin-1-yl)amino]acetateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a suspension of trans-7-chloro-1,2,3,4,10,14b-hexahydro-10-methyldibenzo[b,f]pyrido[1,2-d][1,4]-diazepin-1-ylamine (100 mg, 0.25 mmol) in DMF (2 mL) was added ethyl bromoacetate (56 μl, 0.51 mmol) and triethylamine (107 ul, 0.76 mmol). The resulting reaction mixture was heated to 60° C. and stirred for 5 h. The mixture was poured into water and extracted with ethyl acetate (3×). The organic layers were washed with sat (aq) NaHCO3 and brine. After drying (MgSO4), the solvents were removed under reduced pressure. The crude product was purified on silica with heptane/ethyl acetate 8:2 to afford 80 mg (80%) of the title compound.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. extractionextracted with ethyl acetate (3×)
  3. washThe organic layers were washed
  4. dry with materialAfter drying (MgSO4)
  5. customthe solvents were removed under reduced pressure
  6. customThe crude product was purified on silica with heptane/ethyl acetate 8:2

Quellen und Nachweise

ORD-Eintrag
ord-5f9a424307524be2b55018c39daa4739
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07737136B2

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