Hydrogen Bromide → Palonosetron

HRID 2194981Notes

Reaction equation

HRID 2194981 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([N:9]1[CH2:18][CH:17]3[CH2:19][CH2:20][CH2:21][C:15]4[C:16]3=[C:11]([CH:12]=[CH:13][CH:14]=4)[C:10]1=[O:22])[CH2:2]2.Br>C(O)C>[CH:13]1[CH:12]=[C:11]2[C:10]([N:9]([C@H:3]3[CH:4]4[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]4)[CH2:2]3)[CH2:18][C@H:17]3[CH2:19][CH2:20][CH2:21][C:15](=[C:16]23)[CH:14]=1)=[O:22]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 9882672HCID 9882672, compound

Product 1

HCID 6337614PalonosetronYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
10 °C

Procedure

2-(1-azabicyclo-[2.2.2]oct-3-yl)-2,3,3a,4,5,6-hexahydro-1H-benz[de]isoquinolin-1-one base (30.2 gram, 0.102 mol) was mixed with absolute ethanol (200 ml). The mixture was cooled to about 10° C. and 40% hydrobromic acid (HBr) was added dropwise (23 ml, 0.111 mol). The mixture was stirred at 10° C. for one hour, then concentrated in vacuo. The residue was diluted with ethanol (50 ml) and stirred at 10° C. for one hour. The resulting solid was filtered and dried under reduced pressure to afford 23.1 g of the hydrobromide salt of palonosetron (61% yield) having A/B isomer ratio of 77/22 and purity of 99.2% (as determined by HPLC).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with ethanol (50 ml)
  3. stirringstirred at 10° C. for one hour
  4. filtrationThe resulting solid was filtered
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-71a4384954304e63a2c30927a3577d71
Source dataset
uspto-grants-2012_12
Patent number
US08334388B2

Reaction notes

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