Sodium Hydroxide → HCID 21419614, compound

HRID 1578649Notes

Reaction equation

HRID 1578649 reaction equation
O[C:2]1[CH:15]=[CH:14][C:13]2O[C:11]3[C:6](=[CH:7][C:8]([OH:16])=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.[CH3:17][O-:18].[Na+].Cl.[N:21]1([CH2:27][CH2:28]Cl)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.[OH-:30].[Na+]>ClC1C=CC=CC=1.C(Cl)(Cl)Cl.O.CO>[N:21]1([CH2:27][CH2:17][O:18][C:2]2[CH:15]=[CH:14][C:13]3[O:30][C:11]4[C:6](=[CH:7][C:8]([O:16][CH2:28][CH2:27][N:21]5[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]5)=[CH:9][CH:10]=4)[CH2:5][C:4]=3[CH:3]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 10942334Sodium MethoxideHCID 12340272HCID 12340272, compound

Product 1

HCID 21419614HCID 21419614, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 6212ChloroformSolventHCID 7964ChlorobenzeneSolvent

Procedure

To 20 g (0.093 mole) of 2,7-dihydroxyxanthene in 350 ml of chlorobenzene are added 16.5 g (0.3 mole) of sodium methoxide and 60 ml of methanol. The reaction mixture is stirred and heated during which time the methanol is removed by distillation. The mixture is cooled and 34.7 g (0.26 mole) of 2-piperidinoethyl chloride hydrochloride is added. After refluxing with stirring for 4 hours the mixture is cooled and 100 ml of water plus 10 ml of 50% NaOH solution are added. The mixture is stirred for 15 minutes and 100 ml of chloroform is added. The organic layer which separates is washed with 5% NaOH solution, then with water, dried over anhydrous magnesium sulfate, filtered and concentrated to a solid which is recrystallized from hexane to give 2,7-bis(2-piperidinoethoxy)xanthene.

Workup

  1. customis removed by distillation
  2. temperatureThe mixture is cooled
  3. temperatureAfter refluxing
  4. stirringwith stirring for 4 hours the mixture
  5. temperatureis cooled
  6. stirringThe mixture is stirred for 15 minutes
  7. washThe organic layer which separates is washed with 5% NaOH solution
  8. dry with materialwith water, dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated to a solid which
  11. customis recrystallized from hexane

Sources & evidence

ORD record
ord-feabf6d6dc6d480d824d99c5065c60b4
Source dataset
uspto-grants-1976_02
Patent number
US03937833

Reaction notes

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