Dimethylamine → HCID 71138511, Verbindung

HRID 1852933

Reaktionsgleichung

Reaktionsgleichung von HRID 1852933
C(Cl)(=O)C(Cl)=O.Cl.[CH2:8]([N:15]1[CH2:20][CH2:19][O:18][CH:17]([C:21]([OH:23])=O)[CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[NH:24]([CH3:26])[CH3:25]>ClCCCl.CN(C)C=O>[CH2:8]([N:15]1[CH2:20][CH2:19][O:18][CH:17]([C:21]([N:24]([CH3:26])[CH3:25])=[O:23])[CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

6

Edukt 3

HCID 674DimethylamineHCID 65578Oxalyl chlorideHCID 27763524-Benzylmorpholine-2-carboxylic acid hydrochloride

Produkt 1

HCID 71138511HCID 71138511, VerbindungAusbeute 83,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

Oxalyl chloride (372 μL, 4.27 mmol) was added to a mixture of 4-benzylmorpholine-2-carboxilic acid hydrochloride (1.00 g, 3.88 mmol) and N,N-dimethylformamide (15.0 μL, 0.194 mmol) in DCE (20 mL). The mixture was heated at 65° C. for 3 hours. After cooling to 0° C., Me2NH (2M solution in THF, 9.70 mL, 19.4 mmol) was added. The mixture was stirred at room temperature for 4 hours. The mixture was concentrated and the residue was diluted with water and extracted with EtOAc (3×). The combined organic layers were dried over anhydrous Na2SO4 and concentrated to afford desired product (803 mg, 83.4%) as brown oil.

Aufarbeitung

  1. temperatureAfter cooling to 0° C.
  2. concentrationThe mixture was concentrated
  3. additionthe residue was diluted with water
  4. extractionextracted with EtOAc (3×)
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c1678fe17f3b4520b0d5f80b86a22c23
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962619B2

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