2-Furancarboxylic acid → HCID 15020812, compound

HRID 1493173Notes

Reaction equation

HRID 1493173 reaction equation
[N:1]1([C:7]2[CH:16]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:14]3[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=3[N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[O:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[C:28](O)=[O:29].Cl.CN(C)CCCN=C=NCC>C(Cl)(Cl)Cl>[O:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[C:28]([N:4]1[CH2:3][CH2:2][N:1]([C:7]2[CH:16]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:14]3[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=3[N:8]=2)[CH2:6][CH2:5]1)=[O:29]

Participants

5

Reactant 3

HCID 69192-Furancarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15020770HCID 15020770, compound

Product 1

HCID 15020812HCID 15020812, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 2-(1-piperazinyl)-4-phenyl-5,6,7,8-tetrahydroquinoline (1.2 g), 2-furancarboxylic acid (0.46 g), chloroform (40 ml) and 1-(3-dimethylaminopropyl) 3-ethylcarbodiimide hydrochloride (0.79 g) is stirred at 25° C. for 2 hours. The reaction mixture is washed with water, dried over anhydrous sodium sulfate, and the solvent is distilled off under reduced pressure. The residue is dissolved in toluene and subjected to silica gel column chromatography. The fractions eluted with toluene and toluene-ethyl acetate (9:1) are collected and recrystallized from ethanol to give the desired product (0.4 g), m.p. 128°-130° C.

Workup

  1. washThe reaction mixture is washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationthe solvent is distilled off under reduced pressure
  4. dissolutionThe residue is dissolved in toluene
  5. washThe fractions eluted with toluene and toluene-ethyl acetate (9:1)
  6. customare collected
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-e9ca2f05a85045a0bd04d9f1ef4dfee1
Source dataset
uspto-grants-1991_06
Patent number
US05021421

Reaction notes

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