2,6-Dihydroxy-4-methylquinoline → 4-Methyl-6-{3-[4-(2-propoxybenzyl)-piperazin-1-yl]-propoxy}-2-oxo-1,2-dihydroquinoline

HRID 224773Notes

Reaction equation

HRID 224773 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[NH:5][C:4](=[O:13])[CH:3]=1.[CH2:14]([O:17][C:18]1[CH:34]=[CH:33][CH:32]=[CH:31][C:19]=1[CH2:20][N:21]1[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][CH2:29]Cl)[CH2:23][CH2:22]1)[CH2:15][CH3:16]>>[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH2:29][CH2:28][CH2:27][N:24]3[CH2:25][CH2:26][N:21]([CH2:20][C:19]4[CH:31]=[CH:32][CH:33]=[CH:34][C:18]=4[O:17][CH2:14][CH2:15][CH3:16])[CH2:22][CH2:23]3)[CH:10]=2)[NH:5][C:4](=[O:13])[CH:3]=1

Participants

3

Reactant 2

HCID 6002882,6-Dihydroxy-4-methylquinolineHCID 233304553-[4-(2-Propoxybenzyl)-piperazin-1-yl]-propyl chloride

Product 1

HCID 233304464-Methyl-6-{3-[4-(2-propoxybenzyl)-piperazin-1-yl]-propoxy}-2-oxo-1,2-dihydroquinolineYield 53%

Procedure

In a manner analogous to that described in Example 9, 4-methyl-6-hydroxy-2-oxo-1,2-dihydroquinoline is reacted with 3-[4-(2-propoxybenzyl)-piperazin-1-yl]-propyl chloride. There is obtained 4-methyl-6-{3-[4-(2-propoxybenzyl)-piperazin-1-yl]-propoxy}-2-oxo-1,2-dihydroquinoline in a yield of 53% of theory in the form of an oily base. The corresponding hydrochloride is obtained from an acetone solution of the base, by the addition of ethereal hydrochloric acid, in amorphous fomrm with a melting point of about 140°-145° C.

Sources & evidence

ORD record
ord-8679bafa36554799b98c40748006d5d9
Source dataset
uspto-grants-1980_11
Patent number
US04234585

Reaction notes

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