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

HRID 1830340Notes

Reaction equation

HRID 1830340 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.Cl.C(N=C=NCCCN(C)C)C.[CH3:23][O:24][C:25]1[C:26](=[O:53])[C:27]([CH3:52])=[C:28]([CH2:34][C:35]2[CH:36]=[CH:37][C:38]([O:44][CH2:45][C:46]3[CH:47]=[N:48][CH:49]=[CH:50][CH:51]=3)=[C:39]([CH:43]=2)[C:40](O)=[O:41])[C:29](=[O:33])[C:30]=1[O:31][CH3:32]>C(Cl)Cl>[CH3:23][O:24][C:25]1[C:26](=[O:53])[C:27]([CH3:52])=[C:28]([CH2:34][C:35]2[CH:36]=[CH:37][C:38]([O:44][CH2:45][C:46]3[CH:47]=[N:48][CH:49]=[CH:50][CH:51]=3)=[C:39]([CH:43]=2)[C:40]([N:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][CH2:3][CH2:2]2)=[O:41])[C:29](=[O:33])[C:30]=1[O:31][CH3:32]

Participants

5

Reactant 3

HCID 694601,2,3,4-TetrahydroquinolineHCID 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 22054182N-[5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridylmethyloxy)benzoyl]-1,2,3,4-tetrahydroquinolineYield 39.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,2,3,4-Tetrahydroquinoline (0.126 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, 0.186 mmol, 39%).

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-709483e2fab34f13a099ed210be73ff8
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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