1-Isopropylpiperazine → 1-[2-Hydroxy-3-(4-isopropyl-1-piperazinyl)-4-oxo-2-cyclobuten-1-ylidene]-4-isopropyl-piperazinium hydroxide

HRID 2072286Notes

Reaction equation

HRID 2072286 reaction equation
[NH:1]([C:8]1[C:9](=[O:20])[C:10](=[N:13][C:14]2[CH:19]=CC=CC=2)[C:11]=1[OH:12])[C:2]1[CH:7]=CC=CC=1.[CH:21]([N:24]1[CH2:29][CH2:28]NCC1)([CH3:23])[CH3:22]>>[OH-:12].[OH:12][C:11]1[C:10](=[N+:13]2[CH2:14][CH2:19][N:24]([CH:21]([CH3:22])[CH3:23])[CH2:29][CH2:28]2)[C:9](=[O:20])[C:8]=1[N:1]1[CH2:2][CH2:7][N:1]([CH:8]([CH3:9])[CH3:11])[CH2:2][CH2:7]1

Participants

3

Reactant 2

HCID 780131-IsopropylpiperazineHCID 109783293-Hydroxy-2-(phenylamino)-4-(phenylimino)-2-cyclobuten-1-one

Product 1

HCID 214077881-[2-Hydroxy-3-(4-isopropyl-1-piperazinyl)-4-oxo-2-cyclobuten-1-ylidene]-4-isopropyl-piperazinium hydroxide

Procedure

A mixture of 4.0 grams of 2-anilino-3-hydroxy-4-(phenylimino)-2-cyclobuten-1-one and 3.9 grams of 1-isopropylpiperazine is heated at 200°-206° C. in an atmosphere of dry nitrogen for 30 minutes. The mixture is cooled and the resulting solid is comminuted, washed with anhydrous ethyl ether, dried and then recrystallized from water to give 1-[2-hydroxy-3-(4-isopropyl-1-piperazinyl)-4-oxo-2-cyclobuten-1-ylidene]-4-isopropyl-piperazinium hydroxide inner salt melting at about 194.5°-196.5° C.

Workup

  1. temperatureis heated at 200°-206° C. in an atmosphere of dry nitrogen for 30 minutes
  2. temperatureThe mixture is cooled
  3. customthe resulting solid is comminuted
  4. washwashed with anhydrous ethyl ether
  5. customdried
  6. customrecrystallized from water

Sources & evidence

ORD record
ord-c6989ee03f27499196d869232cfe657b
Source dataset
uspto-grants-1977_09
Patent number
US04051136

Reaction notes

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