Trifluoroacetic acid → N-(4-fluorobenzyl)-N-(3-fluorophenyl)-4-piperidinamine

HRID 1724667Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1724667
[F:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[N:5]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[CH:6]1[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]1.C(O)(C(F)(F)F)=O>ClCCl>[F:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][N:5]([C:4]2[CH:27]=[CH:28][CH:29]=[C:2]([F:1])[CH:3]=2)[CH:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]2)=[CH:25][CH:24]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acid2×HCID 9978463Tert-butyl 4-[3-fluoro(4-fluorobenzyl)anilino]-1-piperidinecarboxylate

Produkt 1

HCID 9882852N-(4-fluorobenzyl)-N-(3-fluorophenyl)-4-piperidinamineAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Tert-butyl 4-[3-fluoro(4-fluorobenzyl)anilino]-1-piperidinecarboxylate 8 (25.5 g) was dissolved in dichloromethane and the solution was cooled to 0° C. TFA (30 ml) was added to the solution and the reaction mixture was stirred at room temperature. After 1 h 30, TFA (20 ml) was added and the reaction mixture was stirred for a further 30 minutes. The solvent was removed under vacuum and the residue was taken up in dichloromethane and water. The aqueous phase was alkalized by addition of NaOH and washed with dichloromethane. The combined organic layers were dried over MgSO4 and concentrated. The crude was purified by chromatography (eluant: CH2Cl2/MeOH/NH4OH 95/5/0.5) to give N-(4-fluorobenzyl)-N-(3-fluorophenyl)-4-piperidinamine (18.4 g) as a free base.

Aufarbeitung

  1. stirringthe reaction mixture was stirred for a further 30 minutes
  2. customThe solvent was removed under vacuum
  3. additionThe aqueous phase was alkalized by addition of NaOH
  4. washwashed with dichloromethane
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated
  7. customThe crude was purified by chromatography (eluant: CH2Cl2/MeOH/NH4OH 95/5/0.5)

Quellen und Nachweise

ORD-Eintrag
ord-dc4933c8a828413c9fe717a3d976430e
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07488741B2

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