Hydrogen Bromide → Eletriptan Hydrobromide

HRID 584853Notes

Reaction equation

HRID 584853 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][CH2:18][S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH:15]=2)[NH:10][CH:9]=1.[BrH:28]>CC(=O)CC>[BrH:28].[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][CH2:18][S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:20])=[O:21])[CH:15]=2)[NH:10][CH:9]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 77993Eletriptan

Product 1

HCID 656631Eletriptan HydrobromideYield 100.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Conditions

Temperature
17.5 °C

Procedure

3-{[1-Methylpyrrolidin-2(R)-yl]methyl}-5-(2-phenylsulphonylethyl)-1H-indole (15 kg) and 2-butanone (204 kg) were charged to a dry, glass-lined vessel. A solution of 48% aqueous hydrobromic acid (6.45 kg) in 2-butanone (63 kg) was added and the resulting slurry was subjected to azeotropic distillation until a volume of 150 litres remained. The reaction mixture was cooled to 17.5° C. and the product was isolated by filtration. The product was washed with 2-butanone (16 kg) to yield the α-polymorphic form of 3-{[1-Methylpyrrolidin-2(R)-yl]methyl}-5-(2-phenylsulphonylethyl)-1H-indole hydrobromide (18.2 kg wet, 17.5 kg when dry, 96.3%).

Workup

  1. distillationthe resulting slurry was subjected to azeotropic distillation until a volume of 150 litres
  2. customthe product was isolated by filtration
  3. washThe product was washed with 2-butanone (16 kg)

Sources & evidence

ORD record
ord-8120f0dbb5fd439fa21327b45e73f5f6
Source dataset
uspto-grants-2005_08
Patent number
US06927296B2

Reaction notes

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