Triethylamine → Benzyl 4-acetylpiperidine-1-carboxylate

HRID 2105521Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2105521
Cl.[C:2]([CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)(=[O:4])[CH3:3].CCN(CC)CC.Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>C(Cl)Cl.O>[C:2]([CH:5]1[CH2:10][CH2:9][N:8]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH2:7][CH2:6]1)(=[O:4])[CH3:3]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 441518974-Acetylpiperidinium chloride

Produkt 1

HCID 19065050Benzyl 4-acetylpiperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

4-Acetylpiperidine hydrochloride (4B-1, 5.0 g, 30.55 mmole) was taken up in CH2Cl2 (150 mL). To this was added Et3N (9.8 mL, 70.27 mmole) and the suspension became a solution. The mixture was cooled to 0° C. to which was added benzyl chloroformate (5.2 mL, 36.66 mmole). After the addition was complete the mixture was warmed to RT. After 18 hr the mixture was diluted with H2O. The layers were separated and the aqueous extracted with CH2Cl2 (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated to afford benzyl 4-acetylpiperidine-1-carboxylate as an off-white solid (4B-2): 1H-NMR (500 MHz, CDCl3) δ 7.35 (m, 5H), 5.13 (s, 2H), 4.18 (bs, 2H), 2.88 (bs, 2H), 2.49 (m, 1H), 2.17 (s, 3H), 1.86 (bs, 2H), 1.55 (m, 2H).

Aufarbeitung

  1. additionAfter the addition
  2. temperaturewas warmed to RT
  3. customThe layers were separated
  4. extractionthe aqueous extracted with CH2Cl2 (3×)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-321701c532a447f5987470bc7e8f4451
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07579355B2

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