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

HRID 530206Notes

Reaction equation

HRID 530206 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(#N)C.C(=O)([O-])[O-].[K+].[K+].[CH2:31]([N:33]([CH3:37])[C:34](Cl)=[O:35])[CH3:32]>C(O)CO>[I-:1].[CH2:31]([N:33]([CH3:37])[C:34]([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:35])[CH3:32]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 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 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
60 °C

Procedure

Mix 7.9 g (0.02 mol) (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 g (0.03 mol) ethyl(methyl)carbamic chloride and 0.1 g of macrogol 400 at room temperature, heat the mixture to 60° C. and let it react for 12 hours. After cooling to room temperature, filter it and reduce the pressure to recover the solvent and receive 10.3 g of red-brown liquid to be directly used in the next reaction.

Workup

  1. customreact for 12 hours
  2. temperatureAfter cooling 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-080269a3bcb044b2b6af52b0dde358fc
Source dataset
uspto-grants-2016_05
Patent number
US09353049B2

Reaction notes

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