Diethyl Malonate → HCID 59822486, compound

HRID 2425762Notes

Reaction equation

HRID 2425762 reaction equation
[CH:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1[CH2:12]O)([CH3:3])[CH3:2].[C:14](OCC)(=[O:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].N1CCCCC1>C1C=CC=CC=1.C(O)(=O)C1C=CC=CC=1>[CH:1]([N:4]1[C:5]2[C:6](=[C:7]([CH3:11])[CH:8]=[CH:9][CH:10]=2)[CH:12]=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:14]1=[O:21])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 7761Diethyl MalonateHCID 8082PiperidineHCID 59822485HCID 59822485, compound

Product 1

HCID 59822486HCID 59822486, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 243Benzoic AcidCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 2-(isopropylamino)-6-methylbenzaldehyde (22.4 g, 127 mmol, step 2 in preparation 2), diethyl malonate (22.3 g, 139 mmol), piperidine (1.29 g, 15.2 mmol), and benzoic acid (572 mg, 4.7 mmol) in benzene (500 mL) was refluxed with stirring for 4 days. After cooling to room temperature, the solvent was removed in vacuo. The residue was chromatographed on a column of silica gel eluting with ethyl acetate/hexane (1:15˜1:2) to give 19.6 g (57%) of the title compound as a yellow solid.

Workup

  1. temperaturewas refluxed
  2. customthe solvent was removed in vacuo
  3. customThe residue was chromatographed on a column of silica gel eluting with ethyl acetate/hexane (1:15˜1:2)

Sources & evidence

ORD record
ord-b5050e1b6f3142f5b32fad60659418d7
Source dataset
uspto-grants-2011_06
Patent number
US07964727B2

Reaction notes

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