Sodium Hydroxide → 1-Benzyl-2,3,9,10,11,12-hexahydro-3-methyl-1H-quino[4,3,2-ef][1,4]benzoxazepine

HRID 1195778Notes

Reaction equation

HRID 1195778 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]([CH3:36])[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.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[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]([CH3:36])[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

7

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 537065391-benzyl-3-methyl-1,3,9,10,11,12-hexahydro-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one

Product 1

HCID 542915511-Benzyl-2,3,9,10,11,12-hexahydro-3-methyl-1H-quino[4,3,2-ef][1,4]benzoxazepineYield 67%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of lithium aluminum hydride in tetrahydrofuran (1M, 12.2 ml) and dry tetrahydrofuran (30 ml) was added aluminum chloride (1.62 g) in portions, with stirring. After five mins, 1-benzyl-3-methyl-1,3,9,10,11,12-hexahydro-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one (4.38 g) was added and stirring was continued overnight. Ethyl acetate (200 ml) and 10% sodium hydroxide solution (200 ml) were added, and the organic layer was separated, dried over anhydrous sodium magnesium sulfate, and concentrated. Recrystallization of the residue from methanol/diethyl ether gave 2.82 g (67%) of product, mp 151.5°-153° C.

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. customthe organic layer was separated
  4. dry with materialdried over anhydrous sodium magnesium sulfate
  5. concentrationconcentrated
  6. customRecrystallization of the residue from methanol/diethyl ether

Sources & evidence

ORD record
ord-5d5be4bae07a45fcba44461c696620ea
Source dataset
uspto-grants-1992_05
Patent number
US05112829

Reaction notes

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