Dimethylformamide → HCID 70925787, Verbindung

HRID 1910519

Reaktionsgleichung

Reaktionsgleichung von HRID 1910519
C(Cl)(=O)C(Cl)=O.Cl.[CH3:8][N:9]1[CH2:14][CH2:13][CH:12]([C:15]([OH:17])=[O:16])[CH2:11][CH2:10]1.CN(C=O)C.[C:23]1([CH:29](O)[CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[CH3:8][N:9]1[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH:29]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:16])[CH2:11][CH2:10]1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 941781,2-DiphenylethanolHCID 27600434-Piperidinecarboxylic acid, 1-methyl-, hydrochloride (1:1)

Produkt 1

HCID 70925787HCID 70925787, VerbindungAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Oxalyl dichloride (141 μl, 1.67 mmol) was added dropwise to a solution of 1-methylpiperidine-4-carboxylic acid hydrochloride (300 mg, 1.67 mmol) in DCM (20 ml) and few drops of DMF (catalytic amount). The reaction was stirred at room temperature for 2 hours. The volatiles were removed under vacuum, and the crude was taken up with pyridine (20 ml). 1,2-Diphenylethanol (331 mg, 1.67 mmol) was added, and the resulting suspension was heated under microwave irradiation at 140° C. for 1 hour. Pyridine was removed under vacuum, and the crude was purified by flash chromatography (DCM/MeOH=97/3 to 94/6) to obtain 1,2-diphenylethyl 1-methylpiperidine-4-carboxylate (200 mg).

Aufarbeitung

  1. customThe volatiles were removed under vacuum
  2. temperaturethe resulting suspension was heated under microwave irradiation at 140° C. for 1 hour
  3. customPyridine was removed under vacuum
  4. customthe crude was purified by flash chromatography (DCM/MeOH=97/3 to 94/6)

Quellen und Nachweise

ORD-Eintrag
ord-b13f5ebe1c75469c810a0348eb917fd9
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604015B2

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