Acetic Anhydride → 1-[4-(4-Aminophenyl)piperidin-1-yl]ethanone

HRID 1428044Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1428044
C([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[CH3:23]CN(CC)CC.C(OC(=O)C)(=O)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([CH:11]2[CH2:12][CH2:13][N:8]([C:6](=[O:5])[CH3:23])[CH2:9][CH2:10]2)=[CH:15][CH:16]=1

Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 22049016tert-butyl 5,6-dihydro-4-(4-nitrophenyl)pyridine-1(2H)-carboxylate

Produkt 1

HCID 591285511-[4-(4-Aminophenyl)piperidin-1-yl]ethanoneAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21863450Trifluoroacetic acid methylene chlorideLösungsmittel

Versuchsvorschrift

A solution of 4-(4-nitro-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (as prepared in the previous step, 304 mg, 1.00 mmol) in a 1:1 mixture of DCM/TFA (10 mL) was stirred at room temperature for 3 h and concentrated. The residue was dried in vacuo overnight, was taken up in CH2Cl2 (10 mL) and was cooled to 0° C. To this solution, Et3N (280 μL, 2 mmol) was added drop wise, followed by acetic anhydride (102 μL, 1 mmol). The resulting mixture was stirred at 0° C. for 1 h and allowed to warm to room temperature. The reaction mixture was washed with brine, and the organic layer was separated, dried and concentrated. The resulting product was reduced to obtain the title compound (143 mg, 65%) using a procedure similar to Example 4, step (d). 1H-NMR (CDCl3; 400 MHz): δ 6.97 (d, 2H, J=8.4 Hz), 6.64 (d, 2H, J=8.4 Hz), 4.75 (m, 1H), 3.93 (m, 1H), 3.13 (m, 3H), 2.66 (m, 2H), 2.12 (s, 3H), 1.84 (m, 2H), 1.57 (m, 2H).

Aufarbeitung

  1. concentrationconcentrated
  2. customThe residue was dried in vacuo overnight
  3. temperaturewas cooled to 0° C
  4. stirringThe resulting mixture was stirred at 0° C. for 1 h
  5. temperatureto warm to room temperature
  6. washThe reaction mixture was washed with brine
  7. customthe organic layer was separated
  8. customdried
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-77a1a483912f425d885e4eb060a92023
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933091B2

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