Hydrogen Bromide → Eletriptan Hydrobromide

HRID 1872745Notes

Reaction equation

HRID 1872745 reaction equation
[BrH:1].[CH3:2][N:3]1[CH2:7][CH2:6][CH2:5][C@@H:4]1[CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][CH2:19][S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH:16]=2)[NH:11][CH:10]=1>CC(C)=O>[BrH:1].[CH3:2][N:3]1[CH2:7][CH2:6][CH2:5][C@@H:4]1[CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][CH2:19][S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)(=[O:21])=[O:22])[CH:16]=2)[NH:11][CH:10]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 77993Eletriptan

Product 1

HCID 656631Eletriptan HydrobromideYield 85.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
2.5 °C

Procedure

62% w/w Hydrobromic acid (1.706 g, 13.07 mmol) was added over 1 hour to a stirred solution of 3-(N-methyl-2(R)-pyrrolidinylmethyl)-5-(2-phenylsulphonylethyl)-1H-indole (5.0 g, 13.07 mmol) in acetone (112 ml) at 0-5° C. After slurrying of the reaction mixture at 0-5° C. for 3 hours, heating under reflux for 2 hours was effected followed by cooling to 0-5° C. and further slurrying for 1 hour at this temperature. Filtration, followed by washing with acetone and drying in vacuo, furnished the title compound (5.18 g), which was identical to that of Example 1.

Workup

  1. temperatureheating
  2. temperatureunder reflux for 2 hours
  3. waitfurther slurrying for 1 hour at this temperature
  4. filtrationFiltration
  5. washby washing with acetone
  6. customdrying in vacuo

Sources & evidence

ORD record
ord-1a688ceb4c6c498fb74cdda0c19054a5
Source dataset
uspto-grants-2000_08
Patent number
US06110940

Reaction notes

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