1,2,3,4-Tetrahydroquinoline → HCID 22054292, compound

HRID 1830338Notes

Reaction equation

HRID 1830338 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:52])[C:27]([CH3:51])=[C:28]([CH2:34][C:35]2[CH:36]=[CH:37][C:38]([O:44][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=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:52])[C:27]([CH3:51])=[C:28]([CH2:34][C:35]2[CH:36]=[CH:37][C:38]([O:44][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=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 22054229HCID 22054229, compound

Product 1

HCID 22054292HCID 22054292, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,2,3,4-Tetrahydroquinoline (0.049 g, 0.367 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.105 g, 0.550 mmol) were added to a methylene chloride solution (10 ml) of 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-phenoxybenzoic acid (0.075 g, 0.183 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 (chloroform:methanol=9:1) to obtain the titled compound (0.050 g, 0.0955 mmol, 52%).

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 (chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-625989ba6d924bb3bcf8475aba90b29d
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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