2-Methylpiperidine → HCID 22054346, compound

HRID 1830339Notes

Reaction equation

HRID 1830339 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][NH:3]1.Cl.C(N=C=NCCCN(C)C)C.[CH3:20][O:21][C:22]1[C:23](=[O:49])[C:24]([CH3:48])=[C:25]([CH2:31][C:32]2[CH:33]=[CH:34][C:35]([O:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=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:49])[C:24]([CH3:48])=[C:25]([CH2:31][C:32]2[CH:33]=[CH:34][C:35]([O:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[C:36]([CH:40]=2)[C:37]([N:3]2[CH2:4][CH2:5][CH2:6][CH2:7][CH:2]2[CH3:1])=[O:38])[C:26](=[O:30])[C:27]=1[O:28][CH3:29]

Participants

5

Reactant 3

HCID 79742-MethylpiperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22054229HCID 22054229, compound

Product 1

HCID 22054346HCID 22054346, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methylpiperidine (0.039 g, 0.391 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.112 g, 0.587 mmol) were added to a methylene chloride solution (5 ml) of 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-phenoxybenzoic acid (0.080 g, 0.196 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 (0.045 g, 0.0919 mmol, 47%).

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-beba9cc420b843ee9b0af5cbbcb80823
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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