4-Methylmorpholine → 1-Benzyl-4-(2-(3,3,3-trifluoropropanoyl)-amino-4-fluoro--phenylamino)-piperidine

HRID 1371507Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1371507
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2N)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:23][C:24]([F:30])([F:29])[CH2:25][C:26](O)=[O:27].C[N:32]1CCOCC1>ClCCl.C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([NH2:32])[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[C:26](=[O:27])[CH2:25][C:24]([F:30])([F:29])[F:23])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 79724-MethylmorpholineHCID 27779723,3,3-Trifluoropropionic acidHCID 211930651-Benzyl-4-(2-amino-4-fluorophenylamino)-piperidine

Produkt 1

HCID 179896591-Benzyl-4-(2-(3,3,3-trifluoropropanoyl)-amino-4-fluoro--phenylamino)-piperidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 9.1 g 1-Benzyl-4-(2-amino-4-fluoro-phenylamino)-piperidine, 2.7 ml 3,3,3-trifluoropropionic acid and 18.6 ml N-methyl-morpholine in 350 ml dichloromethane was dropped 36.4 ml of a 50% solution of PPA in ethyl acetate. The mixture was stirred for 12 h at r.t., extracted 3× with 250 ml water, and the aqueous layers were extracted with 150 ml dichloromethane. After drying the combined organic layers with MgSO4, the solution was evaporated and purified by flash chromatography with dichloromethane/methanol 19:1. The yield was 11.9 g of the desired product.

Aufarbeitung

  1. extractionextracted 3× with 250 ml water
  2. extractionthe aqueous layers were extracted with 150 ml dichloromethane
  3. dry with materialAfter drying the combined organic layers with MgSO4
  4. customthe solution was evaporated
  5. custompurified by flash chromatography with dichloromethane/methanol 19:1

Quellen und Nachweise

ORD-Eintrag
ord-ef320d2ce6af4508b33a29c5fa479849
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157471B2

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