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

HRID 442520Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][O:4][CH:3]([CH2:7][C:8]23[CH2:22][CH:15]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=42)[C:14]2[C:9]3=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:2]1.[CH2:23]=O.Cl>C(O)=O>[CH3:23][N:1]1[CH2:6][CH2:5][O:4][CH:3]([CH2:7][C:8]23[CH2:22][CH:15]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=42)[C:14]2[C:9]3=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 9-(2-morpholinylmethyl)-9,10-dihydro-9,10-methanoanthracene (200 mg), formic acid (600 mg) and 37% formalin (0.25 ml) was stirred at 80° C for 2 hours. 4N Hydrochloric acid was added to the cooled reaction mixture, and the reaction mixture was evaporated to dryness. The residue was diluted with water, basified with aqueous ammonia 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-(4-methyl-2-morpholinylmethyl)-9,10-dihydro-9,10-methanoanthracene, M.P. 136° - 137° C.

Workup

customthe reaction mixture was evaporated to dryness
additionThe residue was diluted with water
extractionextracted with ethyl acetate
washThe ethyl acetate layer was washed with water
dry with materialdried over anhydrous sodium sulfate
customevaporated to dryness

Sources & evidence

ORD record: ord-ff20da63c50b49caac87494fae9fd86e
Source dataset: uspto-grants-1977_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04045560

Reaction notes

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