Sulfuric Acid → HCID 13131688, compound

HRID 435106Notes

Reaction equation

HRID 435106 reaction equation
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([CH2:9][CH2:10][CH2:11][N:12]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:18]3[C:13]2=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:3]1.[S:25](=[O:29])(=[O:28])([OH:27])[OH:26]>CC(C)=O.O>[OH2:26].[S:25]([OH:29])([OH:28])(=[O:27])=[O:26].[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([CH2:9][CH2:10][CH2:11][N:12]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:19]3[C:24]2=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:3]1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 53389Rimcazole

Product 1

HCID 13131688HCID 13131688, compoundYield 189.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To the cis-9-[3-(3,5-dimethyl-1-piperazinyl)propyl]carbazole (10 g) of Example 4 dissolved in warm acetone (100 ml) was slowly added with stirring a solution of sulfuric acid (3.05 g) in water (5 ml), causing immediate precipitation. The slurry was stirred at reflux for 10 min. and then cooled to 20°. The product was collected by filtration and washed with acetone (20 ml). It was reslurried in water (70 ml), filtered, washed with acetone (40 ml) and dried under reduced pressured to give cis-9-[3-(3,5-dimethyl-1-piperazinyl)propyl]carbazole sulfate monohydrate (12.9 g), m.p. 243°-246° (dec.), which had the following analysis:

Workup

  1. additionwas slowly added
  2. customprecipitation
  3. temperatureat reflux for 10 min.
  4. temperaturecooled to 20°
  5. filtrationThe product was collected by filtration
  6. washwashed with acetone (20 ml)
  7. filtrationfiltered
  8. washwashed with acetone (40 ml)
  9. customdried

Sources & evidence

ORD record
ord-39a220b5c37545a1b12496ff0eb29f14
Source dataset
uspto-grants-1983_08
Patent number
US04400383

Reaction notes

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