Methanol → (S)-1-(3-(ethyl(methyl)carbamoyloxy)phenyl)-N,N-dimethyl-N-((S)-1-phenylethyl)ethanaminium iodide

HRID 530210Notes

Reaction equation

[I-:1].[OH: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.CO.C(=O)([O-])[O-].[K+].[K+].[CH2:30]([N:32]([CH3:36])[C:33](Cl)=[O:34])[CH3:31]>C(O)CO>[I-:1].[CH2:30]([N:32]([CH3:36])[C:33]([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)=[O:34])[CH3:31]

Participants

Conditions

Temperature: 60 °C

Procedure

Mix 7.9 g (0.02 mol) of (S)-1-(3-hydroxyphenyl)-N,N-dimethyl-N—((S)-1-phenylethyl)ethanaminium iodide (formula VIII) with 100 ml of methanol, 4.1 g (0.03 mol) of potassium carbonate, 3.6 g (0.03 mol) ethyl(methyl)carbamic chloride and 0.1 g of macrogol 400 at room temperature, heat it to 60° C. and react it for 12 hours. After it is cooled to room temperature, filter it and reduce the pressure to recover the solvent and receive 9.0 g of red-brown liquid to be directly used in the next reaction.

Workup

customreact it for 12 hours
temperatureAfter it is cooled to room temperature
filtrationfilter it
customto recover the solvent
customto be directly used in the next reaction

Sources & evidence

ORD record: ord-55dc97bb3caa45898441804fe4ba47d8
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353049B2

Reaction notes

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