Water → HCID 12331776, compound

HRID 1578647Notes

Reaction equation

HRID 1578647 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-a599b0d0d92f4a7f965a346ec2f065d6
Source dataset
uspto-grants-1976_02
Patent number
US03937833

Reaction notes

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