3-Hydroxy-2-(phenylamino)-4-(phenylimino)-2-cyclobuten-1-one → 1-[2-Hydroxy-3-(cis-2,6-dimethyl-4-propyl-1-piperazinyl)-4-oxo-2-cyclobuten-1-ylidene]-cis-2,6-dimethyl-4-propylpiperazinium hydroxide

HRID 1390359Notes

Reaction equation

HRID 1390359 reaction equation
[NH:1]([C:8]1[C:9](=[O:20])[C:10](=[N:13][C:14]2[CH:19]=CC=C[CH:15]=2)[C:11]=1[OH:12])[C:2]1[CH:7]=CC=C[CH:3]=1.C[C@H]1N[C@@H:26]([CH3:28])[CH2:25][N:24]([CH2:29][CH2:30][CH3:31])C1>>[OH-:12].[OH:12][C:11]1[C:10](=[N+:13]2[C@H:14]([CH3:15])[CH2:19][N:24]([CH2:25][CH2:26][CH3:28])[CH2:29][C@@H:30]2[CH3:31])[C:9](=[O:20])[C:8]=1[N:1]1[C@H:2]([CH3:3])[CH2:7][N:24]([CH2:29][CH2:30][CH3:31])[CH2:25][C@@H:26]1[CH3:28]

Participants

3

Reactant 2

HCID 109783293-Hydroxy-2-(phenylamino)-4-(phenylimino)-2-cyclobuten-1-oneHCID 45099431(3R,5S)-3,5-Dimethyl-1-propylpiperazine

Product 1

HCID 867362961-[2-Hydroxy-3-(cis-2,6-dimethyl-4-propyl-1-piperazinyl)-4-oxo-2-cyclobuten-1-ylidene]-cis-2,6-dimethyl-4-propylpiperazinium hydroxide

Procedure

A mixture of 0.48 grams of 2-anilino-3-hydroxy-4-(phenylimino)-2-cyclobuten-1-one and 0.63 grams of cis-3,5-dimethyl-1-propylpiperazine is heated at 230°-240° C. for 10 minutes. The product is then isolated from the reaction mixture according to the procedure described in Example 5 to give 1-[2-hydroxy-3-(cis-2,6-dimethyl-4-propyl-1-piperazinyl)-4-oxo-2-cyclobuten-1-ylidene]-cis-2,6-dimethyl-4-propylpiperazinium hydroxide inner salt melting at about 218°-227° C. This compound has the following formula ##STR3##

Workup

  1. temperatureis heated at 230°-240° C. for 10 minutes
  2. customThe product is then isolated from the reaction mixture

Sources & evidence

ORD record
ord-fbbb721d2606411bb457833ad269f628
Source dataset
uspto-grants-1979_02
Patent number
US04138566

Reaction notes

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