Triphenylphosphine → 4-[2,2,2-Trifluoro-1-(2-piperidin-1-yl-ethoxy)-1-trifluoromethyl-ethyl]-phenylamine

HRID 557379Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 557379
CCOC(/N=N/C(O[CH2:11][CH3:12])=O)=O.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([OH:29])([C:25]([F:28])([F:27])[F:26])[C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=1.[NH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]1C(O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[F:28][C:25]([F:26])([F:27])[C:20]([C:17]1[CH:16]=[CH:15][C:14]([NH2:13])=[CH:19][CH:18]=1)([O:29][CH2:34][CH2:35][N:30]1[CH2:12][CH2:11][CH2:33][CH2:32][CH2:31]1)[C:21]([F:22])([F:23])[F:24]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 3356821-(Piperidin-2-yl)ethan-1-olHCID 5778012-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-olHCID 5462977Diethyl azodicarboxylate

Produkt 1

HCID 222493264-[2,2,2-Trifluoro-1-(2-piperidin-1-yl-ethoxy)-1-trifluoromethyl-ethyl]-phenylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

DEAD (366 mg, 2.1 mmol) was added drop-wise to the solution of 2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (520 mg, 2 mmol), 2-piperidylethan-1-ol (260 mg, 2 mmol) and PPh3 (550 mg, 2.1 mmol) in THF (10 mL). The mixture was stirred for 2 h. The reaction was partitioned between EtOAc and aqueous NaHCO3 solution and the organic phase was washed with brine. After concentrated in vacuo, the organic residue was purified by flash chromatography on silica to give the title intermediate.

Aufarbeitung

  1. customThe reaction was partitioned between EtOAc and aqueous NaHCO3 solution
  2. washthe organic phase was washed with brine
  3. concentrationAfter concentrated in vacuo
  4. customthe organic residue was purified by flash chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-edbbdc3ccb47424788873680dd2553e3
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058445B2

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