Piperidine → N-[5-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-(4-pyridyl)benzoyl]piperidine

HRID 1245191Notes

Reaction equation

HRID 1245191 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:31])=[C:5]([C:22]([O:29][CH3:30])=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)=[C:11]([CH:15]=1)[C:12]([OH:14])=O.[NH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:1][O:2][C:3]1[C:4]([CH3:31])=[C:5]([C:22]([O:29][CH3:30])=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:16]2[CH:17]=[CH:18][N:19]=[CH:20][CH:21]=2)=[C:11]([CH:15]=1)[C:12]([N:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)=[O:14]

Participants

6

Reactant 3

HCID 8082PiperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 121472835-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-(4-pyridyl)benzoic acid

Product 1

HCID 21919139N-[5-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-(4-pyridyl)benzoyl]piperidineYield 67.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

5-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-(4-pyridyl)benzoic acid (430 mg, 1.0165 mmol) and piperidine (173 mg, 2.0352 mmol) were dissolved in methylene chloride (30 ml), then 4-dimethylaminopyridine (62 mg, 0.5081 mmol) and WSC-HCl (487 mg, 2.5404 mmol) were added thereto and the mixture was stirred at room temperature for 6 hours. The reaction solution was washed with water and dried and the solvent was evaporated therefrom. The residue was purified by silica gel column chromatography (5% methanol-methylene chloride) to give the title compound (334 mg, 0.6816 mmol, 67%).

Workup

  1. washThe reaction solution was washed with water
  2. customdried
  3. customthe solvent was evaporated
  4. customThe residue was purified by silica gel column chromatography (5% methanol-methylene chloride)

Sources & evidence

ORD record
ord-48eac6a33d0646998cce58c69dd4788d
Source dataset
uspto-grants-2006_10
Patent number
US07122543B2

Reaction notes

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