1-Indanone → HCID 14707865, compound

HRID 1387652Notes

Reaction equation

HRID 1387652 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7]1(=O)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8]1>C(Cl)Cl.[Ti].Cl[Ti](Cl)(Cl)Cl>[CH2:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:8]1

Participants

6

Reactant 2

HCID 67351-IndanoneHCID 8082Piperidine

Product 1

HCID 14707865HCID 14707865, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 23963TitaniumCatalystHCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

According to the general method for titanium catalyzed enamine formation of Example 7, dry piperidine (51.4 g, 600 mmol) was treated with TiCl4 (14.35 g, 75.7 mmol) in 400 mL of CH2Cl2 at 0° C. 1-Indanone (10.0 g, 75.6 mmol) was added at this temperature and the reaction mixture was brought to 25° C. 1H NMR analysis of a worked-up aliquot revealed complete conversion to product. Solvent was removed by rotary evaporation and the resulting dark oil and TiO2 residue was triturated with 300 mL of hexane. The solution was filtered through dry Celite and evaporated to afford crude product (20 g dark oil). The product was distilled through a 6″ Vigreaux column to afford pure product (11.01 g, 55.1 mmol) in 73 percent yield as a light yellow oil (98 area percent enamine by GC analysis): bp=143° C. @ 1 mm.

Workup

  1. customwas brought to 25° C
  2. customSolvent was removed by rotary evaporation
  3. customthe resulting dark oil and TiO2 residue was triturated with 300 mL of hexane
  4. filtrationThe solution was filtered
  5. customthrough dry Celite
  6. customevaporated
  7. customto afford crude product (20 g dark oil)
  8. distillationThe product was distilled through a 6″ Vigreaux column

Sources & evidence

ORD record
ord-f3f2a5ed61e34128bee16794b05da150
Source dataset
uspto-grants-2001_07
Patent number
US06268444B1

Reaction notes

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