Piperidine → N-[4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-ylmethyl)benzoyl]piperidine

HRID 496356Notes

Reaction equation

HRID 496356 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:23])[C:5]([CH3:22])=[C:6]([CH2:12][C:13]2[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=2)[C:7](=[O:11])[C:8]=1[O:9][CH3:10].[NH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:4](=[O:23])[C:5]([CH3:22])=[C:6]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:17]([N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[O:18])=[CH:20][CH:21]=2)[C:7](=[O:11])[C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 99488164-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-ylmethyl)benzoic acid

Product 1

HCID 9886316N-[4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-ylmethyl)benzoyl]piperidineYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-ylmethyl)benzoic acid (50 mg, 0.16 mmol) obtained in Example 21 and piperidine (0.021 ml, 0.21 mmol) in methylene chloride (2 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (46 mg, 0.24 mmol), and then the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure and was purified by a silica gel column chromatography (hexane:ethyl acetate=1:2) to yield the title compound (30 mg, 0.08 mmol, yield 50%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customwas purified by a silica gel column chromatography (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-9865333880bd464096e61d1bb838df11
Source dataset
uspto-grants-2005_09
Patent number
US06943196B1

Reaction notes

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