Dimethyl Sulfate → 4-Methyl-4-(2-{[4-(pyren-1-yl)butanoyl]oxy}ethyl)morpholin-4-ium methyl sulfate

HRID 1462996Notes

Reaction equation

[S:1]([O:6]C)([O:4][CH3:5])(=[O:3])=[O:2].[O:8]=[C:9]([O:29][CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1)[CH2:10][CH2:11][CH2:12][C:13]1[C:26]2[C:27]3=[C:28]4[C:23](=[CH:24][CH:25]=2)[CH:22]=[CH:21][CH:20]=[C:19]4[CH:18]=[CH:17][C:16]3=[CH:15][CH:14]=1>CC(C)=O>[CH3:5][O:4][S:1]([O-:6])(=[O:3])=[O:2].[CH3:5][N+:32]1([CH2:31][CH2:30][O:29][C:9](=[O:8])[CH2:10][CH2:11][CH2:12][C:13]2[C:26]3[C:27]4=[C:28]5[C:23](=[CH:24][CH:25]=3)[CH:22]=[CH:21][CH:20]=[C:19]5[CH:18]=[CH:17][C:16]4=[CH:15][CH:14]=2)[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1

Participants

Conditions

Temperature: 50 °C

Procedure

Dimethyl sulfate (6 mls; 0.063M) is added dropwise to a solution of 4-[2-[1-oxo-4-(1-pyrenyl)butoxy]ethyl]morpholine (2.64 grams; 0.006M) in dry acetone (50 mls) at 0° C., and the resulting reaction mixture is then heated at 50° C. for 1.5 hours. The reaction mixture is cooled to ambient temperature and filtered to recover a precipitate of the desired compound which weighs 2.28 grams, after drying in a vacuum oven, and melts at 115°-117° C.

Workup

customthe resulting reaction mixture
temperatureThe reaction mixture is cooled to ambient temperature
filtrationfiltered
customto recover a precipitate of the desired compound which
customafter drying in a vacuum oven, and melts at 115°-117° C.

Sources & evidence

ORD record: ord-98a099d2f6044d4683e3bb4952e7924c
Source dataset: uspto-grants-1984_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04462931

Reaction notes

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