Eletriptan Hydrobromide → Eletriptan hydrobromide monohydrate

HRID 1293156Notes

Reaction equation

HRID 1293156 reaction equation
[CH3:1][N:2]1[C@@H:6]([CH2:7][C:8]2[C:12]3[CH:13]=[C:14]([CH2:17][CH2:18][S:19]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)(=[O:21])=[O:20])[CH:15]=[CH:16][C:11]=3[NH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3]1.[BrH:28]>CC(C)=O.O>[CH3:1][N:2]1[C@@H:6]([CH2:7][C:8]2[C:12]3[CH:13]=[C:14]([CH2:17][CH2:18][S:19]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)(=[O:20])=[O:21])[CH:15]=[CH:16][C:11]=3[NH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3]1.[OH2:20].[BrH:28]

Participants

4

Reactant 1

HCID 656631Eletriptan Hydrobromide

Product 1

HCID 9891365Eletriptan hydrobromide monohydrateYield 188.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

Eletriptan hydrobromide (4.91 g) was dissolved in a mixture of acetone (10 ml) and water (1.85 ml) by heating under reflux. The mixture was treated with acetone (63.6 ml), dropwise over about 20 minutes, and then cooled to ambient temperature. The mixture was granulated overnight (16 hours), cooled to 0–5° C. and granulated at this temperature for a further hour. The resulting solid was filtered, washed with acetone (3 ml) and then dried under reduced pressure and at ambient temperature to give eletriptan hydrobromide monohydrate (4.8 g).

Workup

  1. temperatureby heating
  2. temperatureunder reflux
  3. temperature(16 hours), cooled to 0–5° C.
  4. waitgranulated at this temperature for a further hour
  5. filtrationThe resulting solid was filtered
  6. washwashed with acetone (3 ml)
  7. customdried under reduced pressure and at ambient temperature

Sources & evidence

ORD record
ord-4bbfa4e55eaf4c5ab483f5d445d829f2
Source dataset
uspto-grants-2007_07
Patent number
US07238723B2

Reaction notes

Loading…