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

HRID 530208Notes

Reaction equation

HRID 530208 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.C(=O)([O-])[O-].[K+].[K+].[CH2:28]([N:30]([CH3:34])[C:31](Cl)=[O:32])[CH3:29]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[I-:1].[CH2:28]([N:30]([CH3:34])[C:31]([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:32])[CH3:29]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11240471N-Ethyl-N-methylcarbamoyl chlorideHCID 86712421HCID 86712421, compound2×

Product 1

HCID 86712425(S)-1-(3-(ethyl(methyl)carbamoyloxy)phenyl)-N,N-dimethyl-N-((S)-1-phenylethyl)ethanaminium iodide

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6342AcetonitrileSolvent

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 180 ml of acetonitrile, 4.1 g (0.03 mol) of potassium carbonate, 3.6 (0.03 mol) ethyl(methyl)carbamic chloride and 0.1 g of tetrabutylammonium bromide 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 9.5 g of red-brown liquid to be directly used in the next reaction.

Workup

  1. customreact it for 12 hours
  2. temperatureAfter it is cooled to room temperature
  3. filtrationfilter it
  4. customto recover the solvent
  5. customto be directly used in the next reaction

Sources & evidence

ORD record
ord-e59c03e08c4843459862ec30a5c6a136
Source dataset
uspto-grants-2016_05
Patent number
US09353049B2

Reaction notes

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