Dimethylformamide → (S)-1-(3-methoxyphenyl)-N,N-dimethyl-N-((S)-1-phenylethyl)ethanaminium methyl sulfate

HRID 530200Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@@H:9]([N:11]([CH3:20])[C@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:13])[CH3:10])[CH:6]=[CH:7][CH:8]=1.[CH3:21]N(C)C=O.[S:26]([O:31]C)([O:29][CH3:30])(=[O:28])=[O:27]>C(OCC)(=O)C>[CH3:30][O:29][S:26]([O-:31])(=[O:28])=[O:27].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@@H:9]([N+:11]([CH3:21])([CH3:20])[C@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:13])[CH3:10])[CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Mix 5.5 g (0.02 mol) of (S)-1-(3-methoxyphenyl)-N-methyl-N—((S)-1-phenylethyl)ethanamine (formula IV) with 12 ml N,N-dimethylformamide and 12.6 g (0.1 mol) of dimethyl sulfate at room temperature, heat the mixture to 60° C. for 24 hours. Let it cool to room temperature, and add 100 ml of ethyl acetate. A light yellow solid is produced. Filter and dry it to receive 5.7 g light yellow solid with a yield of 72%.

Workup

temperaturecool to room temperature
customA light yellow solid is produced
filtrationFilter
customdry it

Sources & evidence

ORD record: ord-98a4981450414201aead790c4f1d1c74
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353049B2

Reaction notes

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