4-Methylpiperidine → N-[5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridylmethyloxy)benzoyl]-4-methylpiperidine

HRID 1830341Notes

Reaction equation

HRID 1830341 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl.C(N=C=NCCCN(C)C)C.[CH3:20][O:21][C:22]1[C:23](=[O:50])[C:24]([CH3:49])=[C:25]([CH2:31][C:32]2[CH:33]=[CH:34][C:35]([O:41][CH2:42][C:43]3[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=3)=[C:36]([CH:40]=2)[C:37](O)=[O:38])[C:26](=[O:30])[C:27]=1[O:28][CH3:29]>C(Cl)Cl>[CH3:20][O:21][C:22]1[C:23](=[O:50])[C:24]([CH3:49])=[C:25]([CH2:31][C:32]2[CH:33]=[CH:34][C:35]([O:41][CH2:42][C:43]3[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=3)=[C:36]([CH:40]=2)[C:37]([N:5]2[CH2:6][CH2:7][CH:2]([CH3:1])[CH2:3][CH2:4]2)=[O:38])[C:26](=[O:30])[C:27]=1[O:28][CH3:29]

Participants

5

Reactant 3

HCID 693814-MethylpiperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 220541715-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridylmethyloxy)benzoic Acid

Product 1

HCID 22054306N-[5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridylmethyloxy)benzoyl]-4-methylpiperidineYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methylpiperidine (0.094 g, 0.946 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.272 g, 1.42 mmol) were added to a methylene chloride solution (20 ml) of 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridylmethyloxy)benzoic acid (0.200 g, 0.473 mmol) and the resulting solution was stirred at room temperature for 12 hours. The reaction solution was poured into ice water and then extracted with methylene chloride. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by preparative thin-layer chromatography (hexand:ethyl acetate=9:1) to obtain the titled compound (0.100 g, 0.198 mmol, 42%).

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract was washed with water
  3. customdried
  4. customthe solvent was removed by distillation
  5. customThe obtained residue was purified by preparative thin-layer chromatography (hexand:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-e8e1c5d8845343309908e4a9602f6675
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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