Ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride → Ethyl 3-oxopiperidine-4-carboxylate hydrochloride

HRID 403690Notes

Reaction equation

[ClH:1].C([N:9]1[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:11](=[O:20])[CH2:10]1)C1C=CC=CC=1>C(O)C.[Pd]>[ClH:1].[O:20]=[C:11]1[CH:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:13][CH2:14][NH:9][CH2:10]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of 1.0 g of Pd—C (10 wt. %) was added ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride (10.0 g, 33.58 mmol) (Sigma-Aldrich) dissolved in Ethanol (120 mL). The reaction mixture was then heated at 50° C. under a hydrogen atmosphere (balloon) at atmospheric pressure and followed by HPLC and UPLC-MS. After 4 h at 50° C., the analyses revealed full conversion of the reaction. After cooling to room temperature, the crude mixture was filtered through celite. The celite was washed with EtOH and the filtrate was concentrated in vacuo to give the desired ethyl 3-oxopiperidine-4-carboxylate hydrochloride as an off-white solid (5.84 g, 28.12 mmol, 84% yield). 1HNMR (500 MHz, DMSO-d6): 1.25 (t, J 7.3 Hz, 3H); 2.58 (t, J 6.3 Hz, 2H); 3.26 (t, J 6.3 Hz, 2H); 3.67 (s, 2H), 7.22 (q, J 7.3 Hz, 2H); 9.50 (s, br, 1H); 11.90 (s, br, 1H).

Workup

customconversion of the reaction
temperatureAfter cooling to room temperature
filtrationthe crude mixture was filtered through celite
washThe celite was washed with EtOH
concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-da92b8fd5ded4564a5da0bad090429ef
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748456B2

Reaction notes

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