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Diisopropyl Ether → HCID 178451562, Verbindung

HRID 1355580
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1355580
Cl.[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][C@H:12]([C:14]2[NH:15][CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:18]=2)[NH2:13])=[CH:3]1.[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][C:35](=O)[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].C(OC(C)C)(C)C>C(O)(C)C>[C:19]1([C:17]2[N:18]=[C:14]([C@H:12]3[CH2:11][C:4]4[C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[NH:2][C:3]=4[C:35]4([CH2:36][CH2:37][N:32]([C:30]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:31])[CH2:33][CH2:34]4)[NH:13]3)[NH:15][CH:16]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1
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Komponenten

5

Edukt 3

HCID 7914Diisopropyl EtherHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 178479294HCID 178479294, Verbindung

Produkt 1

HCID 178451562HCID 178451562, VerbindungAusbeute 79,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

To a solution of (1R)-2-(1H-indol-3-yl)-1-(4-phenyl-1H-imidazol-2-yl)-1-ethanamine hydrochloride (14 g, 35 mmol) in isopropanol (210 ml) was added 1-tert-butoxycarbonyl-4-piperidone (35 g, 170 mmol) and the mixture refluxed for about two hours. The solvent was evaporated under reduced pressure. Water (150 ml) was added to the residue followed by 10% NaHCO3 solution until neutral pH and extracted by ethyl acetate (4×50 ml). The combined organic extracts were washed with water (2×50 ml) and dried over MgSO4. The solvent was removed under reduced pressure to afford an oil which solidified on addition of diisopropyl ether (150 ml). The precipitate was collected by filtration, washed with diisopropyl ether and dried to afford 13.5 g of the desired product. Melting point: 118-120° C.

Aufarbeitung

  1. temperaturethe mixture refluxed for about two hours
  2. customThe solvent was evaporated under reduced pressure
  3. additionWater (150 ml) was added to the residue
  4. extractionextracted by ethyl acetate (4×50 ml)
  5. washThe combined organic extracts were washed with water (2×50 ml)
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed under reduced pressure
  8. customto afford an oil which
  9. filtrationThe precipitate was collected by filtration
  10. washwashed with diisopropyl ether
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-571d1c2b625e479fbdac98b516dd6b76
Quelldatensatz
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06586445B1

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