Sodium Hydroxide → HCID 13098067, compound

HRID 1390969Notes

Reaction equation

HRID 1390969 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 an 5% aqueous solution of sodium hydroxide. 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 title 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-2c8cbe30c4f54054aa809dcea7f95cb1
Source dataset
uspto-grants-1979_02
Patent number
US04140790

Reaction notes

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