Aluminum(III) Chloride → HCID 86755330, compound

HRID 1004614Notes

Reaction equation

HRID 1004614 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[CH:5]([N:7]1[CH2:12][CH2:11][C:10](=[CH2:13])[C:9]([CH3:15])([CH3:14])[CH:8]1[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][CH3:24])=[O:6]>ClCCl>[CH:5]([N:7]1[C@H:8]2[C@@:9]([CH3:14])([C:10]([CH3:11])([CH3:13])[C:22]3[CH:21]=[CH:20][CH:19]=[C:18]([O:23][CH3:24])[C:17]=3[CH2:16]2)[CH2:15][CH2:12]1)=[O:6]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 10707423HCID 10707423, compound

Product 1

HCID 86755330HCID 86755330, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 88.0 g (0.66 mol) of aluminium trichloride in 420 mL of absolute dichloromethane is added dropwise, at 0-5° C., a solution of 60.1 g (0.22 mol) of N-formyl-2-(2'-methoxyphenyl) methyl-3,3-dimethyl-4-methylene-piperidine (4) in 200 mL of dichloromethane within 2 h. The mixture is left to react for a further 3 h at 5° C. and then poured onto 800 mL of ice. The organic phase is separated off and the aqueous phase is extracted twice more with 250 mL of dichloromethane. The combined organic phases are dried over MgSO4 and the solvent is eliminated in vacuo. The residue is chromatographed on silica gel (500 g silica gel, solvent: ethyl acetate). 36.0 g (60%) of trans-1-formyl-8-methoxy-3a, 4,4-trimethyl-2,3,3a,4,9,9a-hexahydro-1H-benz[f]indole (5) are obtained as an oil.

Workup

  1. additionis added dropwise, at 0-5° C.
  2. waitThe mixture is left
  3. customto react for a further 3 h at 5° C.
  4. customThe organic phase is separated off
  5. extractionthe aqueous phase is extracted twice more with 250 mL of dichloromethane
  6. dry with materialThe combined organic phases are dried over MgSO4
  7. customThe residue is chromatographed on silica gel (500 g silica gel, solvent: ethyl acetate)

Sources & evidence

ORD record
ord-d686f51d84044d55b7a60e313ba41720
Source dataset
uspto-grants-2000_04
Patent number
US06051583

Reaction notes

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