Sodium Carbonate → 2-(4-Methoxyphenyl)-N-(4-methylbenzyl)-N-(1-(3-(1,3-dihydro-2H-benzimidazol-2-one-1-yl)propyl)piperidine-4yl)acetamide

HRID 354150Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 354150
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([N:12]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)[CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[O:11])=[CH:5][CH:4]=1.Cl[CH2:28][CH2:29][CH2:30][N:31]1[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[NH:33][C:32]1=[O:40].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([N:12]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=2)[CH:13]2[CH2:14][CH2:15][N:16]([CH2:28][CH2:29][CH2:30][N:31]3[C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=4[NH:33][C:32]3=[O:40])[CH2:17][CH2:18]2)=[O:11])=[CH:7][CH:8]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 18104191-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-oneHCID 99465262-(4-Methoxyphenyl)-N-(4-methylbenzyl)-N-(piperidin-4-yl)acetamide

Produkt 1

HCID 101190882-(4-Methoxyphenyl)-N-(4-methylbenzyl)-N-(1-(3-(1,3-dihydro-2H-benzimidazol-2-one-1-yl)propyl)piperidine-4yl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
82 °C

Versuchsvorschrift

50ELH87 (0.05 g, 0.14 mmol, 1 eq.) was transferred to a 4 ml vial and dissolved in 1 ml of acetonitrile. Then, 1-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one (0.032 g, 1.1 eq.), sodium carbonate (0.022 g, 1.1 eq.) and KI (one crystal) were added and the vial was sealed and shaken for 20 h at 82° C. The mixture was extracted with distilled water (pH 10, sodium carbonate) and dichloromethane (3 times) the organic layers were dried with sodium sulfate and concentrated. The title compound was purified by HPLC and evaporated to dryness, forming a trifluoroacetic acid salt. Yield 8.8 mg (12%). UV/MS 100/100 (M+ 527), rt (A, MS) 2.851.

Aufarbeitung

  1. customthe vial was sealed
  2. extractionThe mixture was extracted with distilled water (pH 10, sodium carbonate) and dichloromethane (3 times) the organic layers
  3. dry with materialwere dried with sodium sulfate
  4. concentrationconcentrated
  5. customThe title compound was purified by HPLC
  6. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-bea640ab1acd47c7a4c56e9259385eb8
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06756393B2

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