3-Hydroxy-2-(phenylamino)-4-(phenylimino)-2-cyclobuten-1-one → 1-[2-Hydroxy-3-(cis-3,5-dimethyl-4-propyl-1-piperazinyl)-4-oxo-2-cyclobuten-1-ylidene]-cis-3,5-dimethyl-4-propylpiperazinium hydroxide

HRID 1390358Notes

Reaction equation

HRID 1390358 reaction equation
[NH:1]([C:8]1[C:9](=[O:20])[C:10](=[N:13][C:14]2[CH:19]=[CH:18]C=CC=2)[C:11]=1[OH:12])[C:2]1[CH:7]=[CH:6]C=CC=1.C[C@H]1CN[CH2:25][C@@H:24]([CH3:28])[N:23]1[CH2:29][CH2:30][CH3:31]>>[OH-:12].[OH:12][C:11]1[C:10](=[N+:13]2[CH2:14][C@H:19]([CH3:18])[N:23]([CH2:29][CH2:30][CH3:31])[C@H:24]([CH3:25])[CH2:28]2)[C:9](=[O:20])[C:8]=1[N:1]1[CH2:2][C@H:7]([CH3:6])[N:1]([CH2:2][CH2:7][CH3:6])[C@H:8]([CH3:9])[CH2:11]1

Participants

3

Reactant 2

HCID 109783293-Hydroxy-2-(phenylamino)-4-(phenylimino)-2-cyclobuten-1-oneHCID 28363798(2R,6S)-2,6-Dimethyl-1-propylpiperazine

Product 1

HCID 867362941-[2-Hydroxy-3-(cis-3,5-dimethyl-4-propyl-1-piperazinyl)-4-oxo-2-cyclobuten-1-ylidene]-cis-3,5-dimethyl-4-propylpiperazinium hydroxide

Procedure

A mixture of 1.5 grams of 2-anilino-3-hydroxy-4-(phenylimino)-2-cyclobuten-1-one and 1.9 grams of cis-2,6-dimethyl-1-propylpiperazine is heated at 216°-218° C. for 15 minutes under an atmosphere of dry nitrogen. The product is then isolated as described in Example 5 to give 1-[2-hydroxy-3-(cis-3,5-dimethyl-4-propyl-1-piperazinyl)-4-oxo-2-cyclobuten-1-ylidene]-cis-3,5-dimethyl-4-propylpiperazinium hydroxide inner salt as a pale pinkish brown microcrystalline solid melting at about 202°-204° C.

Workup

  1. temperatureis heated at 216°-218° C. for 15 minutes under an atmosphere of dry nitrogen
  2. customThe product is then isolated

Sources & evidence

ORD record
ord-d55e7381bd9141ef9f5b61ad6953d41e
Source dataset
uspto-grants-1979_02
Patent number
US04138566

Reaction notes

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