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

HRID 442517Notes

Reaction equation

HRID 442517 reaction equation
O=[C:2]1[CH:7]([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)[O:6][CH2:5][CH2:4][NH:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCOCC1.C(OCC)(=O)C>[NH:3]1[CH2:4][CH2:5][O:6][CH:7]([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)[CH2:2]1

Participants

6

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydride2×HCID 214150352-[(9,10-Methanoanthracen-9(10H)-yl)methyl]morpholin-3-one

Product 1

HCID 214150272-[(9,10-Methanoanthracen-9(10H)-yl)methyl]morpholine

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 9-(3-oxo-2-morpholinylmethyl)-9,10-dihydro-9,10-methanoanthracene (100 mg) and lithium aluminum hydride (50 mg) in dioxane was stirred at 60° - 70° C. for 3 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-(2-morpholinylmethyl)-9,10-dihydro-9,10-methanoanthracene, M.P. 183° - 189° C. Recrystallization gave colorless crystals, M.P. 189° - 190° C.

Workup

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

Sources & evidence

ORD record
ord-755e1b3c8a314e4899ca2ad2cf4da049
Source dataset
uspto-grants-1977_08
Patent number
US04045560

Reaction notes

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