Trifluoroacetic acid → 2-Amino-N-(1-benzylpiperidin-4-yl)-3-fluorobenzamide

HRID 1177796Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1177796
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=2[NH:24]C(=O)OC(C)(C)C)=[O:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:24][C:18]1[C:19]([F:23])=[CH:20][CH:21]=[CH:22][C:17]=1[C:15]([NH:14][CH:11]1[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][CH2:10]1)=[O:16]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 59639684tert-Butyl 2-(1-benzylpiperidin-4-ylcarbamoyl)-6-fluorophenylcarbamate

Produkt 1

HCID 211021192-Amino-N-(1-benzylpiperidin-4-yl)-3-fluorobenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 2-(1-benzylpiperidin-4-ylcarbamoyl)-6-fluorophenylcarbamate (67.0 g, 157 mmol) in dichloromethane (700 mL) at 0° C. was added trifluoroacetic acid (100 mL). The ice bath was removed and the reaction stirred at room temperature overnight. The reaction was concentrated and partitioned between ethyl acetate and saturated sodium bicarbonate. The aqueous was extracted with ethyl acetate (2×), which were washed with water (3×), then brine, dried over magnesium sulfate, and concentrated to give 47.6 g (93%) as a white solid which was used without purification. Mass spec.: 328.33 (MH)+.

Aufarbeitung

  1. customThe ice bath was removed
  2. concentrationThe reaction was concentrated
  3. custompartitioned between ethyl acetate and saturated sodium bicarbonate
  4. extractionThe aqueous was extracted with ethyl acetate (2×), which
  5. washwere washed with water (3×)
  6. dry with materialbrine, dried over magnesium sulfate
  7. concentrationconcentrated
  8. customto give 47.6 g (93%) as a white solid which
  9. customwas used without purification

Quellen und Nachweise

ORD-Eintrag
ord-37eeb294f3864d56a59b2da9caacaa03
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842808B2

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