Hydrogen Bromide → Eletriptan Hydrobromide

HRID 1872744Notes

Reaction equation

HRID 1872744 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>COCCOC>[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 88%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

49% w/w Hydrobromic acid (27.86 ml, 0.25 mol) was added over 1 hour to a stirred solution of 3-(N-methyl-2(R)-pyrrolidinylmethyl)-5-(2-phenylsulphonylethyl)-1H-indole (92.86 g, 0.24 mol) in 1,2-dimethoxyethane (2.08 1) at about 5° C. The cooling bath was removed and the resulting slurry was allowed to granulate by stirring at room temperature for a further 18 hours. Filtration, followed by washing with 1,2-dimethoxyethane and drying in vacuo, afforded the required product (97.9 g) as a solid, m.p. 150-151° C. Found: C,56.77; H,5.87; N,5.85. C22H26N2O2S; HBr requires C,57.02; H,5.87; N,6.04%.

Workup

  1. customThe cooling bath was removed
  2. filtrationFiltration
  3. washby washing with 1,2-dimethoxyethane
  4. customdrying in vacuo

Sources & evidence

ORD record
ord-dc533acf119545aeac32b6a74d881a13
Source dataset
uspto-grants-2000_08
Patent number
US06110940

Reaction notes

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