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

HRID 530209Notes

Reaction equation

HRID 530209 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:22](=[O:25])([O-])[O-].[K+].[K+].C1O[CH2:44][CH2:43]OCCOCCOCCOCCOC1.[C:46](#[N:48])C>>[I-:1].[CH2:43]([N:48]([CH3:46])[C:22]([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:25])[CH3:44]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 86712421HCID 86712421, compound2×

Product 1

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

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 g (0.03 mol) ethyl(methyl)carbamic chloride chloride and 0.1 g 18-crown-6 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 9.9 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-ae12098b2e464a6099429a3f82ceb0ca
Source dataset
uspto-grants-2016_05
Patent number
US09353049B2

Reaction notes

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