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Cesium carbonate → HCID 57355799, Verbindung

HRID 481034
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 481034
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[NH:16][C:15]2=[O:23])[CH2:10][CH2:9]1)=O)(C)(C)C.Br[CH2:25][CH2:26][CH2:27][N:28]1[C:32](=[O:33])[C:31]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]2[C:29]1=[O:38].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[NH:8]1[CH2:9][CH2:10][CH:11]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]([CH2:25][CH2:26][CH2:27][N:28]3[C:32](=[O:33])[C:31]4=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]4[C:29]3=[O:38])[C:15]2=[O:23])[CH2:12][CH2:13]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 21611N-3-BromopropylphthalimideHCID 13046891tert-Butyl 4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidine-1-carboxylate

Produkt 1

HCID 57355799HCID 57355799, VerbindungAusbeute 113,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of Compound 9 (42.2 g, 0.13M), prepared in Example 9, and N-(3-bromopropyl)phthalimide (35 g, 0.13M) were dissolved in DMF (300 ml). Cesium carbonate (100 g, 0.3M) was added in one portion and the resulting heterogenous mixture heated in an 80° C. oil bath for 16 hours. The mixture was cooled to room temperature and the DMF removed under reduced pressure. The residue was poured into ice water (800 ml) and stirred at room temperature overnight. The white solid precipitates were collected and dried to give the desired product (60 g, 92%). The BOC group was removed by treatment of a solution of the compound in methylene chloride (500 ml) with excess trifluoroacetic acid (46 ml, 0.6M). The mixture was stirred at room temperature overnight and evaporated to dryness under reduced pressure. The resulting white solids were washed with diethyl ether and dried to give the desired TFA salt. m.p. 173-175° C. 1H NMR (300 MHz, DMSO-d6) δ8.79 (m, 1H; 8.54 (m, 1H); 7.82 (s, 4H); 7.35 (m, 1H); 7.25 (m, 1H); 7.07-6.90 (m, 2H); 4.55 (m, 1H); 3.90 (t, J=7 Hz, 2H); 3.63 (t, J=7 Hz, 2H); 3.42 (m, 2H); 3.15 (m, 2H); 2.60(m, 2H); 2.07 (m, 2H); 1.90 (m, 2H). MS: m/z (MH+) 405

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. customthe DMF removed under reduced pressure
  3. additionThe residue was poured into ice water (800 ml)
  4. customThe white solid precipitates
  5. customwere collected
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-91ff835a0438404e95362b79baa33558
Quelldatensatz
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06653478B2

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