Hydrochloric Acid → HCID 19037321, Verbindung

HRID 263383

Reaktionsgleichung

Reaktionsgleichung von HRID 263383
[Cl:1][C:2]1[C:8]([O:9][CH:10]([CH3:12])[CH3:11])=[CH:7][C:5]([NH2:6])=[C:4]([F:13])[CH:3]=1.C[Al](C)C.[NH:18]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:19]1[C:20](OCC)=[O:21].Cl>C(Cl)Cl.O>[Cl:1][C:2]1[C:8]([O:9][CH:10]([CH3:11])[CH3:12])=[CH:7][C:5]([NH:6][C:20]([CH:19]2[CH2:25][CH2:26][CH2:27][CH2:28][NH:18]2)=[O:21])=[C:4]([F:13])[CH:3]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 27517Ethyl piperidine-2-carboxylateHCID 158649Benzenamine, 4-chloro-2-fluoro-5-(1-methylethoxy)-HCID 16682925Trimethylaluminum

Produkt 1

HCID 19037321HCID 19037321, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

The product of Example 1, Step A (4.25 g, 26.37 mmol) was dissolved in CH2Cl2 (200 mL). A solution of 2.0M trimethylaluminum (52.75 mmol) was added dropwise under nitrogen at 0° C. The resultant mixture was stirred at room temperature overnight. Ethyl pipecolinate (4.15 g) was added dropwise to the mixture and the mixture was stirred for 2 days. To the reaction mixture 6N HCl (100 mL) was added dropwise at 0° C. 200 mL of H2O was added, followed by the addition of 150 mL of methylene chloride. The aqueous layer was separated and basicified to pH 10 with 50% aqueous NaOH. 500 mL of CH2Cl2 was added. The organic layer was separated, dried over MgSO4, filtered and evaporated to dryness under vacuum to give the title compound of Step A as a white solid, 4.7 g. m.p. 96°-98° C. 1H NMR (CDCl3): δ9.25 (br s,1H), 8.17 (d,1H), 7.13 (d,1H) 4.58 (m,1H), 3.20 (M,1H), 3.10 (m,1H), 2.79 (m,1H), 2.00 (m,1H), 1.89 (m,2H), 1.60-1.40 (m,4H), 1.36 (d,6H).

Aufarbeitung

  1. customThe aqueous layer was separated
  2. addition500 mL of CH2Cl2 was added
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c7dc60f6c06a446ca17c0516941f6f12
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05643855

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