Piperidine → HCID 22054247, compound

HRID 1830296Notes

Reaction equation

HRID 1830296 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.C(N=C=NCCCN(C)C)C.[CH3:19][O:20][C:21]1[C:22](=[O:43])[C:23]([CH3:42])=[C:24]([CH2:30][C:31]2[CH:32]=[CH:33][C:34]([O:40][CH3:41])=[C:35]([CH:39]=2)[C:36](O)=[O:37])[C:25](=[O:29])[C:26]=1[O:27][CH3:28]>C(Cl)Cl>[CH3:19][O:20][C:21]1[C:22](=[O:43])[C:23]([CH3:42])=[C:24]([CH2:30][C:31]2[CH:32]=[CH:33][C:34]([O:40][CH3:41])=[C:35]([CH:39]=2)[C:36]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:37])[C:25](=[O:29])[C:26]=1[O:27][CH3:28]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22054158HCID 22054158, compound

Product 1

HCID 22054247HCID 22054247, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Piperidine (0.027 g, 0.318 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.091 g, 0.477 mmol) were added to a methylene chloride solution (5 ml) of 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-methoxybenzoic acid (0.055 g, 0.159 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 (ethyl acetate) to obtain the titled compound (0.0175 g, 0.0423 mmol, 27%).

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 (ethyl acetate)

Sources & evidence

ORD record
ord-b3f29cf0e2dd4031bd136f9d53a5a966
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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