Hydrogen Bromide → Eletriptan Hydrobromide

HRID 843969Notes

Reaction equation

HRID 843969 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 93.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

49% w/w Hydrobromic acid (432 mg, 0.3 ml, 2.6 mmol) was added to a stirred solution of 3-(N-methyl-2(R)-pyrrolidinylmethyl)-5-(2-phenylsulphonylethyl)-1H-indole (1.0 g, 2.6 mmol) in acetone (10 ml) at room temperature. After a further 15 minutes, the reaction mixture was evaporated under reduced pressure to give a yellow liquid; the residual water therein was then azeotropically removed using 2-propanol. The resulting cloudy, yellowish oil (1.55 g) was triturated with ether and then dissolved in hot 2-propanol (25 ml); this solution, on cooling, provided the title compound (1.13 g) as a pale yellow crystalline solid after filtration, washing with 2-propanol and drying in vacuo, m.p. 165-170° C. Found: C,56.67; H,5.78; N,5.82. C22H26N2O2S; HBr requires C,57.02; H,5.87; N,6.04%.

Workup

  1. customthe reaction mixture was evaporated under reduced pressure
  2. customto give a yellow liquid
  3. customthe residual water therein was then azeotropically removed
  4. customThe resulting cloudy, yellowish oil (1.55 g) was triturated with ether
  5. dissolutiondissolved in hot 2-propanol (25 ml)
  6. temperaturethis solution, on cooling

Sources & evidence

ORD record
ord-b9ce7b3190fd4cc598e5e84b82991df0
Source dataset
uspto-grants-2002_04
Patent number
US06380226B1

Reaction notes

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