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Hydrochloric Acid → 1-(2-(4-(6-Methoxy-2-(5-methylthiophen-2-yl)naphthalen-1-yloxy)phenoxy)ethyl)piperidine hydrochloride

HRID 445200
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 445200
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=2)[C:8]=1[O:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[CH:22][CH:21]=1)(=O)=O.[CH3:37][C:38]1[S:42][C:41](B(O)O)=[CH:40][CH:39]=1.[F-].[Cs+].C(=O)(O)[O-].[Na+].[ClH:53]>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>[ClH:53].[CH3:18][O:17][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[C:8]([O:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][N:29]3[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]3)=[CH:22][CH:21]=1)=[C:7]([C:41]1[S:42][C:38]([CH3:37])=[CH:39][CH:40]=1)[CH:16]=[CH:15]2
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 25953Cesium fluorideHCID 516892Sodium BicarbonateHCID 2734374(5-Methylthiophen-2-yl)boronic acidHCID 116133766-Methoxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)naphthalen-2-yl trifluoromethanesulfonate

Produkt 1

HCID 67308050
1-(2-(4-(6-Methoxy-2-(5-methylthiophen-2-yl)naphthalen-1-yloxy)phenoxy)ethyl)piperidine hydrochloride
Ausbeute 90,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 75806TricyclohexylphosphineKatalysator2×HCID 167845palladium(II) acetateKatalysator2×HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Suspend 6-methoxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)naphthalen-2-yl trifluoromethanesulfonate (398.8 g; 758.8 mmol), 5-Methyl-2-thiopheneboronic Acid (224 g; 1.58 mol), and cesium fluoride (300 g; 1.97 mol) in acetonitrile (12 L). Degas the resulting suspension via gas inlet tube for 30 minutes while heating to 50° C. Treat the mixture with tricyclohexylphosphine (8 g; 28.5 mmol) and degas for 10 minutes, then treat with palladium (II) acetate (4 g; 17.8 mmol), degas for an additional 5 minutes, and stir overnight at 80° C. Add tricyclohexylphosphine (8 g; 28.5 mmol) and palladium (II) acetate (4 g; 17.8 mmol) and heat the mixture for an additional 8 hours, then allow the solution to slowly cool overnight. Filter the cooled solution through a large glass frit and concentrate the filtrate. Slurry the residue and filter cake in water (4 L) and ethyl acetate (8 L), then transfer to a separatory funnel and treat with saturated aqueous sodium bicarbonate (300 g; 3.57 mol). Stir vigorously for 10 minutes, then separate the layers. Wash the organic layer with saturated aqueous sodium bicarbonate, brine, and dry over MgSO4 overnight. Filter the mixture, and treat the filtrate with HCl (4N in dioxane, 200 mL, 800 mmol). Stir the resulting slurry 60 minutes; then filter to obtain the title compound (352 g; 690.06 mmol). LRMS (m/z): 474 (M+1-HCl).

Aufarbeitung

  1. customDegas the resulting suspension via gas inlet tube for 30 minutes
  2. customdegas for 10 minutes
  3. customdegas for an additional 5 minutes
  4. customto slowly cool overnight
  5. filtrationFilter the cooled solution through a large glass frit
  6. concentrationconcentrate the filtrate
  7. filtrationfilter cake in water (4 L)
  8. customethyl acetate (8 L), then transfer to a separatory funnel
  9. stirringStir vigorously for 10 minutes
  10. customseparate the layers
  11. washWash the organic layer with saturated aqueous sodium bicarbonate, brine
  12. dry with materialdry over MgSO4 overnight
  13. filtrationFilter the mixture
  14. stirringStir the resulting slurry 60 minutes
  15. filtrationthen filter

Quellen und Nachweise

ORD-Eintrag
ord-5b2e4b8a9b0f4338a8dec977e68ff488
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08476300B2

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