Water → HCID 12151521, compound

HRID 1058220Notes

Reaction equation

HRID 1058220 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.[C:11]1(=O)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12]1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.O>C1(C)C=CC=CC=1>[CH2:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([N:2]2[CH2:3][CH2:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:1]2)=[CH:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 67351-IndanoneHCID 70461,2,3,4-TetrahydroisoquinolineHCID 14812Phosphorus oxide (P4O10)

Product 1

HCID 12151521HCID 12151521, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Tetrahydroisoquinoline (Aldrich Chemical, 18.0 g, 135.1 mmol), 1-indanone (10.0 g, 75.1 mmol) and P2O5 (2.30 g, 16.1 mmol) in 150 mL of toluene were stirred under nitrogen and refluxed for 10 h with water removal via a Dean Stark apparatus. Upon cooling a large amount of fine white powder precipitated (as amine phosphate salts). The dark green solution was filtered under N2 through a medium porosity frit and assayed by NMR after tolune removal (about 85:15 mole ratio of product to ketone). Solvent was evaporated and indanone/amine (about 3.0 g) was removed in vacuo (90-160° C. at 0.5 mm Hg, 76 Pa). The process was stopped and the crude enamine residue recovered under inert atmosphere, giving 18.0 g of dark red-green oil, 95 percent yield. The crude product was analyzed by 1H and 13C NMR and showed less than 2 percent mole ketone.

Workup

  1. temperatureUpon cooling a large amount of fine white powder
  2. customprecipitated (as amine phosphate salts)
  3. filtrationThe dark green solution was filtered under N2 through a medium porosity frit
  4. customafter tolune removal (about 85:15 mole ratio of product to ketone)
  5. customSolvent was evaporated
  6. customindanone/amine (about 3.0 g) was removed in vacuo (90-160° C. at 0.5 mm Hg, 76 Pa)
  7. customthe crude enamine residue recovered under inert atmosphere

Sources & evidence

ORD record
ord-2cbc2f3be3984fa79525f28048372051
Source dataset
uspto-grants-2003_02
Patent number
US06515155B1

Reaction notes

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