Aluminum(III) Chloride → HCID 53732297, compound

HRID 981946Notes

Reaction equation

HRID 981946 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[CH2:11]([N:18]1[C:24]2=[C:25]3[C:30](=[N:31][C:32]4=[CH:33][CH:34]=[CH:35][C:22](=[C:23]24)[O:21][CH:20]([CH2:36][CH3:37])[C:19]1=O)[CH2:29][CH2:28][CH2:27][CH2:26]3)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>O1CCCC1>[CH2:11]([N:18]1[C:24]2=[C:25]3[C:30](=[N:31][C:32]4=[CH:33][CH:34]=[CH:35][C:22](=[C:23]24)[O:21][CH:20]([CH2:36][CH3:37])[CH2:19]1)[CH2:29][CH2:28][CH2:27][CH2:26]3)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 53995652HCID 53995652, compound

Product 1

HCID 53732297HCID 53732297, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of lithium aluminum hydride in tetrahydrofuran (1M, 11.75 ml) and dry tetrahydrofuran (30 ml) was added aluminum chloride (1.57 g) in portions. The mixture was stirred for five mins. 1-Benzyl-3-ethyl-1,3,9,10,11,12-hexahydro-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one (4.37 g) was added and stirring was continued for three hrs. The reaction mixture was quenched with ethyl acetate (200 ml), 10% sodium hydroxide solution (200 ml) was added, and the organic layer was separated, dried over anhydrous magnesium sulfate and concentrated. Trituration of the residue with pentane followed by recrystallization from methanol gave 2.86 g (68%) of product, mp 147.5°-149° C.

Workup

  1. stirringstirring
  2. waitwas continued for three hrs
  3. customThe reaction mixture was quenched with ethyl acetate (200 ml), 10% sodium hydroxide solution (200 ml)
  4. additionwas added
  5. customthe organic layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customTrituration of the residue with pentane followed by recrystallization from methanol

Sources & evidence

ORD record
ord-3f437a43871d48bca52306f93761da4e
Source dataset
uspto-grants-1991_02
Patent number
US04994452

Reaction notes

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