Water → HCID 178523336, compound

HRID 1089122Notes

Reaction equation

HRID 1089122 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[OH:12])[N:5]=[CH:4][C:3]=1[C:13]([OH:15])=O.[C:16]1([CH:22]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[N:23]2[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][CH2:31][CH2:32][NH2:33])[CH2:25][CH2:24]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CS(C)=O>[C:34]1([CH:22]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:23]2[CH2:24][CH2:25][N:26]([CH2:29][CH2:30][CH2:31][CH2:32][NH:33][C:13]([C:3]3[CH:4]=[N:5][C:6]4[C:11]([C:2]=3[OH:1])=[C:10]([OH:12])[CH:9]=[CH:8][CH:7]=4)=[O:15])[CH2:27][CH2:28]2)[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

5

Reactant 3

HCID 962WaterHCID 139569931-(4-Aminobutyl)-4-(diphenylmethyl)piperazineHCID 178524716HCID 178524716, compound

Product 1

HCID 178523336HCID 178523336, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

N,N'-Carbonyldiimidazole (1.2 g) is added to a solution of 4,5-dihydroxyquinoline-3-carboxylic acid (0.7 g), which is prepared according to the method described in Japanese Patent First Publication No. 65874/1981, in dry dimethyl sulfoxide (30 ml) and the mixture is stirred at room temperature for 30 minutes. 4-(4-Diphenylmethyl-1-piperazinyl)butylamine (2.2 g) is added to the reaction mixture and the mixture is stirred at room temperature for 6 hours, and thereto is added water (about 200 ml), and the mixture is extracted with chloroform. The organic layer is dried over anhydrous magnesium sulfate and the solvent is distilled off. The residue is subjected to silica gel column chromatography, followed by elution with chloroform - methanol (30 : 1). The obtained crystals are recrystallized from isopropyl alcohol to give the desired compound (0.72 g). m.p. 215° to 218° C.

Workup

  1. customis prepared
  2. extractionthe mixture is extracted with chloroform
  3. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  4. distillationthe solvent is distilled off
  5. washfollowed by elution with chloroform - methanol (30 : 1)
  6. customThe obtained crystals are recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-a142bd64f53347f9ab9ce5ff40d1c648
Source dataset
uspto-grants-1990_10
Patent number
US04965266

Reaction notes

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