Morpholine → HCID 72187884, Verbindung

HRID 515162Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 515162
Br[C:2]1[CH:18]=[C:17]([CH3:19])[C:5]([C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[O:7])=[C:4]([O:20][CH3:21])[CH:3]=1.[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN1CCCC1=O.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][NH:8][C:6](=[O:7])[C:5]2[C:17]([CH3:19])=[CH:18][C:2]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:3][C:4]=2[O:20][CH3:21])=[CH:11][CH:12]=1

Komponenten

8

Edukt 4

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 86699733HCID 86699733, Verbindung

Produkt 1

HCID 72187884HCID 72187884, VerbindungAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a stirred solution of 4-bromo-N-[(4-chlorophenyl)-methyl]-2-methoxy-6-methyl-benzamide (0.37 g, 1.02 mmol) in N-methyl-2-pyrrolidone (1 ml) is added morpholine (0.10 ml, 1.20 mmol) at RT. The reaction mixture is degassed and flushed with argon for 30 min followed by addition of caesium carbonate (0.49 g, 1.52 mmol). The reaction mixture is heated to 40° C. At this temperature are added tris(dibenzylideneacetone)dipalladium(0) (0.009 g, 0.01 mmol) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.019 g, 0.030 mmol) and stirred at 110° C. for 16 h. After completion of the reaction (monitored by TLC), the mixture is diluted with water (20 ml) and extracted with ethyl acetate (3×20 ml). The organic layer is washed with water (20 ml), brine (20 ml), dried over anhydrous sodium sulfate and evaporated to get the crude product, which is purified by column chromatography (silica gel, 20% acetone/hexane) to yield N-[(4-chlorophenyl)-methyl]-2-methoxy-6-methyl-4-morpholin-4-yl-benzamide (example 10) (0.11 g, 0.29 mmol, 29%). [M+H]+ 375.2.

Aufarbeitung

  1. customThe reaction mixture is degassed
  2. customflushed with argon for 30 min
  3. customAfter completion of the reaction (monitored by TLC)
  4. extractionextracted with ethyl acetate (3×20 ml)
  5. washThe organic layer is washed with water (20 ml), brine (20 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated
  8. customto get the crude product, which
  9. customis purified by column chromatography (silica gel, 20% acetone/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-3b5514f2e5494bd6abecad4905a3676d
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108936B2

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