Aluminum(III) Chloride → 2,3,9,10,11,12-Hexahydro-1-propyl-1H-quino[4,3,2-ef][1,4]benzoxazepine

HRID 981927Notes

Reaction equation

HRID 981927 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[CH2:11]([N:14]1[C:20]2=[C:21]3[C:26](=[N:27][C:28]4=[CH:29][CH:30]=[CH:31][C:18](=[C:19]24)[O:17][CH2:16][C:15]1=O)[CH2:25][CH2:24][CH2:23][CH2:22]3)[CH2:12][CH3:13]>O1CCCC1>[CH2:11]([N:14]1[C:20]2=[C:21]3[C:26](=[N:27][C:28]4=[CH:29][CH:30]=[CH:31][C:18](=[C:19]24)[O:17][CH2:16][CH2:15]1)[CH2:25][CH2:24][CH2:23][CH2:22]3)[CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 53716832HCID 53716832, compound

Product 1

HCID 540056442,3,9,10,11,12-Hexahydro-1-propyl-1H-quino[4,3,2-ef][1,4]benzoxazepineYield 71.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of lithium aluminum hydride in tetrahydrofuran (1.0M, 14.2 ml) and dry tetrahydrofuran (30 ml) was added aluminum chloride (1.89 g) in portions. The mixture was stirred for five mins, 1,3,9,10,11,12-hexahydro-1-propyl-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one (4.2 g) was added, and stirring was continued overnight. The reaction mixture was quenched with ethyl acetate (200 ml), 10% sodium hydroxide solution (200 ml) was added, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was recrystallized from pentane/diethyl ether to yield 2.85 g (71%) of product, mp 74.5°-75.5° C.

Workup

  1. stirringstirring
  2. waitwas continued overnight
  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 materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated
  9. customThe residue was recrystallized from pentane/diethyl ether

Sources & evidence

ORD record
ord-cdf201c870e24ed7829d494ddbb0d8bc
Source dataset
uspto-grants-1991_02
Patent number
US04994452

Reaction notes

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