Sodium Hydroxide → HCID 13098067, compound

HRID 1413547Notes

Reaction equation

HRID 1413547 reaction equation
Cl.Cl.[CH2:3]([N:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][O:16][C:17]([CH:19]2[C:32]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:26][C:25]3[C:20]2=[CH:21][CH:22]=[CH:23][CH:24]=3)=[O:18])[CH2:9][CH2:8]1)[CH2:4][CH2:5][CH3:6].[OH-].[Na+]>>[CH2:3]([N:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][O:16][C:17]([CH:19]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=3[O:26][C:27]3[C:32]2=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:18])[CH2:9][CH2:8]1)[CH2:4][CH2:5][CH3:6]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 15572561HCID 15572561, compound

Product 1

HCID 13098067HCID 13098067, compoundYield 82.5%

Conditions

Temperature
0 °C

Procedure

5 g of 3-(4-butyl-piperazin-1-yl)-1-(xanthene-9-carbonyloxy)-propane dihydrochloride, prepared as described in Example 2, are admixed with 20 ml of a 5% aqueous solution of sodium hydroxide, and the alkaline solution is extracted with 3×20 ml of ethyl ether. The etheral extracts are combined, dried over sodium sulfate, filtered, and the filtrate is evaporated. The residue is dissolved in 25 ml of acetone, and 3.5 g of methyl iodide are added to the solution. The reaction mixture is refluxed for 15 minutes and then cooled to 0° C. The crystalline product is filtered off and recrystallized from 30 ml of ethanol. 3.5 g of the named compound are obtained; m.p.: 188°-190° C.

Workup

  1. extractionthe alkaline solution is extracted with 3×20 ml of ethyl ether
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customthe filtrate is evaporated
  5. dissolutionThe residue is dissolved in 25 ml of acetone
  6. addition3.5 g of methyl iodide are added to the solution
  7. temperatureThe reaction mixture is refluxed for 15 minutes
  8. filtrationThe crystalline product is filtered off
  9. customrecrystallized from 30 ml of ethanol

Sources & evidence

ORD record
ord-50346124b25749f695f4f6447da4dc66
Source dataset
uspto-grants-1981_02
Patent number
US04250310

Reaction notes

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