Ethyl benzoylformate → N-(1-benzyl-4-piperidinyl)phenyl-glyoxylic acid amide

HRID 566375

Reaction equation

[C:1]1([C:7](=[O:13])[C:8]([O:10]CC)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:17][CH2:16]1>C(O)C>[CH2:21]([N:18]1[CH2:19][CH2:20][CH:15]([NH:14][C:8](=[O:10])[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:13])[CH2:16][CH2:17]1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Added to 4.28 g of ethyl phenylglyoxylate were 9.12 g of 4-amino-1-benzylpiperidine. The mixture was heated and stirred at 120° C. for 3 hours on an oil bath. Thereafter, ethanol formed was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel, thereby obtaining 6.3 g (yield: 81.4%) of N-(1-benzyl-4-piperidinyl)phenyl-glyoxylic acid amide.

Workup

temperatureThe mixture was heated
distillationwas distilled off under reduced pressure
customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-647897c87c744c8bb37ca0405e06145b
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06174900B1

Linked notes

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