Phosphoric Acid → HCID 22465554, compound

HRID 1935989Notes

Reaction equation

HRID 1935989 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH-].[K+].[CH3:12][N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C:14]1=O.P(=O)(O)(O)O>COCCOC.CCOCC>[CH:1]1([C:16]2([CH:1]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH:3]=[CH:2]3)[CH2:17][CH2:18][N:13]([CH3:12])[CH2:14][CH2:15]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

7

Reactant 4

HCID 1004Phosphoric AcidHCID 7219IndeneHCID 13603N-Methyl-2-piperidoneHCID 14797Potassium Hydroxide

Product 1

HCID 22465554HCID 22465554, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

0.25 mole of indene was added within 0.5 hours under vigorous stirring to the suspension of 15 g of KOH powder in 150 ml of DME. The mixture was heated to reflux. Then 0.1 mole of 1-methylpiperidone dissolved in 10 ml of DME was added dropwise within 0.5 hours and the mixture was stirred under reflux for additional 2 hours. The resulting mixture was cooled, treated by 200 ml of diluted phosphoric acid till the neutralization and by 100 ml of Et2O. The organic layer was separated and treated by 20% excess of diluted acetic acid. The aqueous layer was separated, washed twice with Et2O and neutralissed with a diluted alkali solution. The 4,4-bis-indenyl-1-methyl-piperidine was extracted with CH2Cl2, the organic layer was separated, the solvent was removed and the residue was recrystallized from hexane. The yield of the 4,4-bis-indenyl-1-1methyl-piperidine was 67%. 1H NMR (C6D6, 30° C.) δ: 7.57(d,2H); 7.20(d,2H); 7.04(t,2H); 6.97(t,2H); 6.28(s,2H); 3.08(s,4H); 2.58(m,4H); 2.44(m,4H); 2.17(s,3H).

Workup

  1. temperatureThe mixture was heated to reflux
  2. additionwas added dropwise within 0.5 hours
  3. temperatureunder reflux for additional 2 hours
  4. temperatureThe resulting mixture was cooled
  5. customThe organic layer was separated
  6. additiontreated by 20% excess of diluted acetic acid
  7. customThe aqueous layer was separated
  8. washwashed twice with Et2O
  9. extractionThe 4,4-bis-indenyl-1-methyl-piperidine was extracted with CH2Cl2
  10. customthe organic layer was separated
  11. customthe solvent was removed
  12. customthe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-091ea4348d024418b4ab8831d2d1ffde
Source dataset
uspto-grants-2002_05
Patent number
US06388118B1

Reaction notes

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