Triethylamine → Methyl 3-(4-oxopiperidin-1-yl)propanoate

HRID 1357825Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1357825
O.Cl.[O:3]=[C:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.Br[CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14].C([O-])([O-])=O.[K+].[K+].CCN(CC)CC>CC(C)=O>[O:3]=[C:4]1[CH2:9][CH2:8][N:7]([CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH2:6][CH2:5]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 76934Methyl 3-bromopropanoateHCID 2723901Piperonylamine

Produkt 1

HCID 18187970Methyl 3-(4-oxopiperidin-1-yl)propanoateAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a suspension of 4-oxopiperidine hydrochloride monohydrate (10.0 g, 65.1 mmol) and methyl 3-bromopropanoate (7.8 ml, 71.6 mmol) in acetone (100 ml) was added K2CO3 (9.9 g, 71.6 mmol) and Et3N (9.1 ml, 65.3 mmol). The mixture was refluxed for 24 hours. The solid was removed by filtration and the solvent was evaporated. The residue was partitioned between EtOAc and H2O. The organic extracts were combined and dried over Na2SO4. The solvent was evaporated to give the title compound (15.0 g, 27.0 mmol, 42%) as an oil. 1H NMR (300 MHz, CDCl3) δ 3.70 (s, 3H), 2.75-2.85 (mult, 6H), 2.52-2.57 (mult, 2H), 2.42-2.46 (mult, 4H).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 24 hours
  2. customThe solid was removed by filtration
  3. customthe solvent was evaporated
  4. customThe residue was partitioned between EtOAc and H2O
  5. dry with materialdried over Na2SO4
  6. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-220fcefd2d934c3c8285c1d6a6718815
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06593347B2

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