Aluminum(III) Chloride → HCID 15101112, compound

HRID 704591Notes

Reaction equation

HRID 704591 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].O1[C:15]2([CH2:20][CH2:19][CH:18]([CH2:21][C:22]([N:24]3[CH2:29][CH:28]=[C:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH2:26][CH2:25]3)=O)[CH2:17][CH2:16]2)[O:14]CC1>O1CCCC1.C(OCC)C>[C:30]1([C:27]2[CH2:28][CH2:29][N:24]([CH2:22][CH2:21][CH:18]3[CH2:19][CH2:20][C:15](=[O:14])[CH2:16][CH2:17]3)[CH2:25][CH:26]=2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

6

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 15101123HCID 15101123, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15101112HCID 15101112, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirring suspension of lithium aluminum hydride (9.24 g) in 250 ml of dry tetrahydrofuran under nitrogen is added dropwise a solution of aluminum chloride (10.82 g) in 250 ml of diethyl ether. The mixture is stirred at room temperature for 20 minutes and a solution of 1-(1,4-dioxaspiro-[4,5]-dec-8-ylacetyl)-1,2,3,6-tetrahydro-4-phenylpyridine (27.70 ) (Example Ia) in 500 ml of tetrahydrofuran is added dropwise. The resulting mixture is stirred at room temperature for 12 hours. The reaction is quenched by careful addition of 10 ml of water. After 30 minutes, 44 g of a 25% solution of sodium hydroxide is added dropwise and the mixture stirred for one additional hour. The inorganic salts are filtered through Celite and the filtrate evaporated in vacuo, taken up into 250 ml of a 10% solution of hydrochloric acid and 250 ml of acetone and refluxed for eight hours. The solution is cooled, concentrated in vacuo to remove the acetone, made basic with ammonium hydroxide, and extracted with chloroform (2×250 ml). The organic extracts are pooled, dried over magnesium sulfate, and evaporated to give a semisolid residue which is triturated with 100 ml of diethyl ether and filtered. The title compound is obtained (16.82 g) as a light yellow solid; mp 94°-96° C.

Workup

  1. stirringThe resulting mixture is stirred at room temperature for 12 hours
  2. customThe reaction is quenched by careful addition of 10 ml of water
  3. waitAfter 30 minutes
  4. addition44 g of a 25% solution of sodium hydroxide is added dropwise
  5. stirringthe mixture stirred for one additional hour
  6. filtrationThe inorganic salts are filtered through Celite
  7. customthe filtrate evaporated in vacuo
  8. temperaturerefluxed for eight hours
  9. temperatureThe solution is cooled
  10. concentrationconcentrated in vacuo
  11. customto remove the acetone
  12. extractionextracted with chloroform (2×250 ml)
  13. dry with materialdried over magnesium sulfate
  14. customevaporated
  15. customto give a semisolid residue which
  16. customis triturated with 100 ml of diethyl ether
  17. filtrationfiltered

Sources & evidence

ORD record
ord-5791e4bff26b4dbb88b72e98254ac0cc
Source dataset
uspto-grants-1991_01
Patent number
US04988699

Reaction notes

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