Formic Acid → 9-gamma-Morpholinopropyl-9,10-dihydro-9,10-methanoanthracene

HRID 2198642Notes

Reaction equation

HRID 2198642 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(O)=O.[CH:10]1[C:23]2[C:22]3([CH2:25][CH2:26][CH:27]=O)[CH2:24][CH:15]([C:16]4[C:21]3=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:14]=2[CH:13]=[CH:12][CH:11]=1>O>[O:4]1[CH2:5][CH2:6][N:1]([CH2:27][CH2:26][CH2:25][C:22]23[CH2:24][CH:15]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=42)[C:14]2[C:23]3=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 8083MorpholineHCID 15586332HCID 15586332, compound

Product 1

HCID 130690769-gamma-Morpholinopropyl-9,10-dihydro-9,10-methanoanthracene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of morpholine (870 mg) and formic acid (460 mg) heated at 60° C. was added β-(9,10-dihydro-9,10-methano-9-anthryl)propionaldehyde (50 mg). The resultant mixture was stirred at 60° C. for 30 minutes and at 80° C. for 1.5 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous sodium sulfate and evaporated to dryness to give 9-γ-morpholinopropyl-9,10-dihydro-9,10-methanoanthracene, which was converted into its hydrochloride. M.P. 173°-176.5° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-ad246fd93b614303870de3cc39f889eb
Source dataset
uspto-grants-1982_11
Patent number
US04358620

Reaction notes

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