2,4-Dimethoxybenzoic acid → HCID 24695582, compound

HRID 552328Notes

Reaction equation

Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=O.[OH:9]N1C2C=CC=CC=2N=N1.[CH3:19][O:20][C:21]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:22]=1[C:23](O)=[O:24].C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[CH3:19][O:20][C:21]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:22]=1[C:23]([N:2]1[CH2:7][CH2:6][C:5](=[O:9])[CH2:4][CH2:3]1)=[O:24]

Participants

Conditions

Temperature: 0 °C

Procedure

Piperidone hydrochloride (3.0 g, 19.5 mmol) dissolved in DMF (25 ml), N,N-diiso-propylcarbodiimide (8.2 g, 65.1 mmol) and 1-hydroxybenzotriazole (8.8 g, 65.1 mmol) were added at 0° C. to a solution of 2,4-dimethoxybenzoic acid (11.8 g, 65.1 mmol) in DMF (25 ml) and the mixture was stirred at 0° C. for 3 h and subsequently at RT for 2 d. Aqueous 1M Na2CO3 solution (20 ml) was added to the reaction mixture and it was extracted with EA (3×20 ml). After drying of the combined organic phases, the solvent was removed and the residue was purified by means of column chromatography. The product 1-(2,4-dimethoxybenzoyl)piperidin-4-one was obtained in a yield of 2.7 g (39%).

Workup

extractionwas extracted with EA (3×20 ml)
customAfter drying of the combined organic phases
customthe solvent was removed
customthe residue was purified by means of column chromatography

Sources & evidence

ORD record: ord-248183ed923c4a07819c23ec61a3afe4
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951815B2

Reaction notes

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