Water → HCID 12331776, compound

HRID 441635Notes

Reaction equation

HRID 441635 reaction equation
O.[OH-].[Na+].[OH:4][C:5]1[CH:18]=[CH:17][C:8]2[S:9][C:10]3[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][C:11]=3[C:7]=2[CH:6]=1.[ClH:19].[N:20]1([CH2:26][CH2:27][CH2:28][Cl:29])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>C1(C)C=CC=CC=1>[ClH:29].[ClH:19].[N:20]1([CH2:26][CH2:27][CH2:28][O:16][C:13]2[CH:14]=[CH:15][C:10]3[S:9][C:8]4[CH:17]=[CH:18][C:5]([O:4][CH2:28][CH2:27][CH2:26][N:20]5[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]5)=[CH:6][C:7]=4[C:11]=3[CH:12]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 79624N-(3-chloropropyl)piperidine hydrochlorideHCID 1204339HCID 1204339, compound

Product 1

HCID 12331776HCID 12331776, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 200 ml of water containing 12.0 g (0.3 mole) of sodium hydroxide and 8.5 g (0.039 mole) of 2,8-dihydroxydibenzothiophene are added 200 ml of toluene and 19.8 g (0.1 mole) of 3-piperidinopropyl chloride hydrochloride, and the heterogeneous reaction mixture is stirred and heated to reflux for 16 hours. After cooling, the organic layer is washed with water, dried over magnesium sulfate, and concentrated in vacuo. The free base is chromatographed on alumina, using chloroform as the eluant. After removing the chloroform from the fraction collected, the oily residue is dissolved in ether and treated with ethereal hydrogen chloride. The resulting solid is purified by two recrystallizations from methanol-butanone to give 2,8-bis(3-piperidinopropoxy)dibenzothiophene dihydrochloride, M.P. 240°-242° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 hours
  3. temperatureAfter cooling
  4. washthe organic layer is washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe free base is chromatographed on alumina
  8. customAfter removing the chloroform from the fraction
  9. customcollected
  10. dissolutionthe oily residue is dissolved in ether
  11. additiontreated with ethereal hydrogen chloride
  12. customThe resulting solid is purified by two recrystallizations from methanol-butanone

Sources & evidence

ORD record
ord-2e367d1593ee4af19c7be653f86fe942
Source dataset
uspto-grants-1977_08
Patent number
US04041165

Reaction notes

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