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

HRID 530203Notes

Reaction equation

[CH3:1][N:2]([C@H:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:13])[C@H:3]([C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)[CH3:4].[CH3:20]N(C)C=O.[S:25]([O:30]C)([O:28][CH3:29])(=[O:27])=[O:26]>C(OCC)(=O)C>[CH3:29][O:28][S:25]([O-:30])(=[O:27])=[O:26].[OH:11][C:7]1[CH:6]=[C:5]([C@@H:3]([N+:2]([CH3:20])([CH3:1])[C@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:13])[CH3:4])[CH:10]=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Mix 5.1 g (0.02 mol) of 3-[(S)-1-(methyl-[(S)-1-phenylethyl]amino)ethyl]phenol (formula V) with 10 ml N,N-dimethylformamide and 12.6 g (0.1 mol) of dimethyl sulfate at room temperature, and heat the mixture to 60° C. for 10 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 7.0 g light yellow solid with a yield of 85%.

Workup

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

Sources & evidence

ORD record: ord-9417b946ffac4766a801152e94aec93b
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353049B2

Reaction notes

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