Diethyl 2-(2-cyanoethyl)-2-phenylmalonate → Ethyl 2-oxo-3-phenylpiperidine-3-carboxylate

HRID 53667Notes

Reaction equation

HRID 53667 reaction equation
[C:1]1([C:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])([C:12](OCC)=[O:13])[CH2:8][CH2:9][C:10]#[N:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)C.[Pt](=O)=O>[C:1]1([C:7]2([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:8][CH2:9][CH2:10][NH:11][C:12]2=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 10017046Diethyl 2-(2-cyanoethyl)-2-phenylmalonate

Product 1

HCID 305256Ethyl 2-oxo-3-phenylpiperidine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-phenyl 4,4 diethoxycarbonyl butyronitrile (16.49 g) in dry ethanol (250 ml) was hydrogenated over platinum dioxide at 50 psi for 8 hours. The catalyst was filtered off and the solvent removed under reduced pressure. Product recrystallised from ether (14.1 g) mp 79°-80° C. 1H NMR (360 MHz, CDCl3) δH 1.24 (t, 3H, J=7.0 Hz, CH2CH3), 1.71 (2H, m, CH2CH2CH2C), 2.32 (1H, m, CH2CH2CHHC), 2.68 (1H, m, CH2CH2CHHC), 3.36 (2H, m, CH2CH2CH2C), 4.22 (2H, q, J=7.0 Hz, CH2CH3), 6.26 (1H, bs, NH), 7.30 (5H, m, Ar H). m/z (CI+) 248 (M+1)+.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent removed under reduced pressure
  3. customProduct recrystallised from ether (14.1 g) mp 79°-80° C

Sources & evidence

ORD record
ord-f59e677c4f0142ae9f97177cc1c1d23c
Source dataset
uspto-grants-1997_04
Patent number
US05620989

Reaction notes

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