1-Chloro-4-(trifluoromethyl)benzene → 1-[4-(Trifluoromethyl)phenyl]piperidine

HRID 1596836

Reaktionsgleichung

Reaktionsgleichung von HRID 1596836
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.CC([O-])(C)C.[Na+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N:12]1([C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Komponenten

6

Edukt 3

HCID 73941-Chloro-4-(trifluoromethyl)benzeneHCID 8082PiperidineHCID 23676156Sodium t-butoxide

Produkt 1

HCID 4250921-[4-(Trifluoromethyl)phenyl]piperidineAusbeute 23,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

The general procedure from Example 1 was followed using 4-chlorobenzotrifluoride (650 mg, 3.6 mmol) and piperidine (258 mg, 3.0 mmol) with Pd2(dba)3 (55 mg, 0.081 mmol) and (Me3C)2PH(O) (21.0 mg, 0.126 mmol) and NaOtBu (432 mg, 4.5 mmol) in 6.0 mL of toluene. After 48 h, the reaction mixture was chromatographed with 5% ethyl acetate/hexane to give 161 mg (23% yield) of 4-piperidinobenzotrifluoride. It was >95% pure by 1H NMR and GC/MS. 1H NMR (500 MHz, CDCl3): δ 7.36 (d, J=8.78 Hz, 2H), 6.82 (d, J=8.79 Hz, 2H), 3.18 (m, 4H), 1.60 (m, 4H), 1.54 (m, 2H) ppm. 13C NMR (125 MHz, CDCl3): d 153.7, 127.6, 126.3, 114.5, 49.2, 25.4, 24.2 ppm. MS: Calculated for C12H14F3N(M+): 229.1. Found: 230.2 (M++H).

Aufarbeitung

  1. customthe reaction mixture was chromatographed with 5% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-75fb21128153415099446192b2dcd126
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06291722B1

Verknüpfte Notizen

Wird geladen…