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2,4-Dimethoxybenzoic acid → 1-(2,4-Dimethoxybenzoyl)piperidin-4-one

HRID 552328
Notes
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Reaction equation

HRID 552328 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 70522,4-Dimethoxybenzoic acidHCID 10340Sodium CarbonateHCID 757711-HydroxybenzotriazoleHCID 20088740Piperidin-2-one--hydrogen chloride (1/1)

Product 1

HCID 246955821-(2,4-Dimethoxybenzoyl)piperidin-4-one

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
2×

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

  1. extractionwas extracted with EA (3×20 ml)
  2. customAfter drying of the combined organic phases
  3. customthe solvent was removed
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes