Hydrogen Bromide → HCID 86712421, compound

HRID 530201Notes

Reaction equation

HRID 530201 reaction equation
[I-:1].C[O:3][C:4]1[CH:5]=[C:6]([C@@H:10]([N+:12]([CH3:22])([CH3:21])[C@H:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:14])[CH3:11])[CH:7]=[CH:8][CH:9]=1.COS([O-])(=O)=O.COC1C=C([C@@H]([N+](C)(C)[C@H](C2C=CC=CC=2)C)C)C=CC=1.Br>CC(C)=O>[I-:1].[OH:3][C:4]1[CH:5]=[C:6]([C@@H:10]([N+:12]([CH3:22])([CH3:21])[C@H:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:14])[CH3:11])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 86712417(S)-1-(3-methoxyphenyl)-N,N-dimethyl-N-((S)-1-phenylethyl)ethanaminium iodideHCID 86712420(S)-1-(3-methoxyphenyl)-N,N-dimethyl-N-((S)-1-phenylethyl)ethanaminium methyl sulfate

Product 1

HCID 86712421HCID 86712421, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Mix 8.2 g (0.02 mol) of (S)-1-(3-methoxyphenyl)-N,N-dimethyl-N—((S)-1-phenylethyl)ethanaminium iodide (formula VI) with 15 ml (content greater than 40% by mass) hydrobromic acid, heat and reflux the mixture for 10 hours. Let it cool to room temperature, and add 120 ml of acetone. A pale yellow solid is produced. Filter and dry it to receive 6.4 g pale yellow solid with a yield of 80%.

Workup

  1. temperatureheat
  2. temperaturereflux the mixture for 10 hours
  3. customA pale yellow solid is produced
  4. filtrationFilter
  5. customdry it

Sources & evidence

ORD record
ord-d13c18d1f05f4bbab917460bb45117bd
Source dataset
uspto-grants-2016_05
Patent number
US09353049B2

Reaction notes

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