Water → 2-[(9,10-Methanoanthracen-9(10H)-yl)methyl]-4-methylmorpholine

HRID 442516Notes

Reaction equation

HRID 442516 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][O:5][CH:4]([CH2:8][C:9]23[CH2:23][CH:16]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=42)[C:15]2[C:10]3=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:3]1=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCOCC1.C(OCC)(=O)C>[CH3:1][N:2]1[CH2:7][CH2:6][O:5][CH:4]([CH2:8][C:9]23[CH2:23][CH:16]([C:15]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=42)[C:17]2[C:22]3=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:3]1

Participants

6

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydride2×HCID 214150342-[(9,10-Methanoanthracen-9(10H)-yl)methyl]-4-methylmorpholin-3-one

Product 1

HCID 214150012-[(9,10-Methanoanthracen-9(10H)-yl)methyl]-4-methylmorpholine

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 9-(4-methyl-3-oxo-2-morpholinylmethyl)-9,10-dihydro-9,10-methanoanthracene (170 ml) and lithium aluminum hydride (100 mg) in dioxane was stirred at 60° - 70° C. for 6 hours. Excess lithium aluminum hydride was decomposed by addition of water. The reaction mixture was diluted with ethyl acetate, dried over anhydrous sodium sulfate and evaporated to dryness to give 9-(4-methyl-2-morpholinylmethyl)-9,10-dihydro-9,10-methanoanthracene, M.P. 136° - 137° C.

Workup

  1. dry with materialdried over anhydrous sodium sulfate
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-7bb3c8f30c3d4030838f676fb353c7a3
Source dataset
uspto-grants-1977_08
Patent number
US04045560

Reaction notes

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