Water → HCID 12331750, compound

HRID 1578646Notes

Reaction equation

HRID 1578646 reaction equation
O.[OH-].[Na+].[OH:4][C:5]1[CH:18]=[CH:17][C:8]2[O: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[O: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 458258HCID 458258, compound

Product 1

HCID 12331750HCID 12331750, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 200 ml of water containing 13.0 g (0.33 mole) of sodium hydroxide and 12.0 g (0.06 mole) of 2,8-dihydroxydibenzofuran are added 250 ml of toluene and 29.7 g (0.15 mole) of 3-piperidinopropyl chloride hydrochloride, and the heterogeneous reaction mixture is heated to reflux with stirring for 24 hours. When cool, the organic layer is washed with water, dried over magnesium sulfate then concentrated in vacuo. The remaining oily residue is dissolved in ether and treated with ethereal HCl to give the desired product which is recrystallized twice from methanol-ethyl acetate yielding 2,8-bis(3-piperidonopropoxy)dibenzofuran dihydrochloride, M.P. 245°-246.5°C.

Workup

  1. temperaturethe heterogeneous reaction mixture is heated
  2. temperatureto reflux
  3. temperatureWhen cool
  4. washthe organic layer is washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationthen concentrated in vacuo
  7. dissolutionThe remaining oily residue is dissolved in ether
  8. additiontreated with ethereal HCl

Sources & evidence

ORD record
ord-0abc3333de884729abbb5614c8a7d4c5
Source dataset
uspto-grants-1976_02
Patent number
US03937833

Reaction notes

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