Aluminum(III) Chloride → HCID 13986144, compound

HRID 255894Notes

Reaction equation

HRID 255894 reaction equation
C(O[C:4](=O)[NH:5][CH2:6][CH:7]([C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][CH2:12][N:13]2[C:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[OH:8])C.[H-].[Li+].[Al+3].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-]>O1CCOCC1.C(OCC)(=O)C>[CH3:4][NH:5][CH2:6][CH:7]([C:9]1[C:10]2[CH2:11][CH2:12][N:13]([CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:14]=2[CH:15]=[CH:16][CH:17]=1)[OH:8]

Participants

6

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 20145780HCID 20145780, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13986144HCID 13986144, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 113 g of the compound of Step C in 1,130 ml of dioxane was added slowly with stirring under an inert atmosphere to a suspension of 110 g of aluminium-lithium hydride and 55 g of aluminium chloride in 1,700 ml of dioxane. After 1 hour of stirring betweeen 80° C. and 50° C. and cooling to 10° C., the excess hydride was destroyed with an ammonium chloride-dioxane-water mixture. The resulting mixture was diluted with water, filtered, and the filtrate was concentrated by eliminating about 1,000 ml of solvent. After adding water and extracting with methylene chloride, the extracts were washed with water saturated with sodium chloride, dried and evaporated to dryness to obtain 95 g of crude product. The crude product was refluxed with stirring in 1 liter of ethyl acetate and 8.5 g of insoluble matter corresponding to the hydrochloride of the expected product were filtered off and melted at ≃179° C. The filtrate was concentrated hot to 400 ml, left to crystallize to obtain 55.19 g of 2,3-dihydro-α-[(methylamino)-methyl]-1-benzyl-1H-indol-4-methanol melting at ≃112° C.

Workup

  1. temperaturecooling to 10° C.
  2. customthe excess hydride was destroyed with an ammonium chloride-dioxane-water mixture
  3. additionThe resulting mixture was diluted with water
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. additionAfter adding water
  7. extractionextracting with methylene chloride
  8. washthe extracts were washed with water saturated with sodium chloride
  9. customdried
  10. customevaporated to dryness
  11. customto obtain 95 g of crude product
  12. filtration8.5 g of insoluble matter corresponding to the hydrochloride of the expected product were filtered off
  13. custommelted at ≃179° C
  14. concentrationThe filtrate was concentrated hot to 400 ml
  15. waitleft
  16. customto crystallize

Sources & evidence

ORD record
ord-3305a784260243b884a7e7d857d7054f
Source dataset
uspto-grants-1987_10
Patent number
US04699907

Reaction notes

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