Hydrochloric Acid → Topotecan Hydrochloride

HRID 1801860

Reaction equation

HRID 1801860 reaction equation
[CH3:1][CH2:2][C@@:3]1([OH:31])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:29](=[CH:30][C:4]1=2)[C:28]1[N:27]=[C:17]2[CH:18]=[CH:19][C:20]([OH:26])=[C:21]([CH2:22][N:23]([CH3:25])[CH3:24])[C:16]2=[CH:15][C:14]=1[CH2:13]3)=[O:11].[ClH:32]>CO>[CH3:1][CH2:2][C@@:3]1([OH:31])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:29](=[CH:30][C:4]1=2)[C:28]1[N:27]=[C:17]2[CH:18]=[CH:19][C:20]([OH:26])=[C:21]([CH2:22][N:23]([CH3:24])[CH3:25])[C:16]2=[CH:15][C:14]=1[CH2:13]3)=[O:11].[ClH:32]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 60700Topotecan

Product 1

HCID 60699Topotecan Hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
27.5 °C

Procedure

10 grams of topotecan base was suspended in 100 ml Methanol, and 2.4 ml HCl was added at 25-30° C. and stirred for 1 hour at 25-30° C., the suspension was further chilled to 10-15° C. and stirred for 1 hour at 10-15° C. and filtered, washed with 5 ml of methanol. The product was dried in vacuum at 25-30° C. for 5 hours, followed by drying at 30-35° C. for 36 hours to get 8.0 g of topotecan hydrochloride form A.

Workup

  1. temperaturethe suspension was further chilled to 10-15° C.
  2. stirringstirred for 1 hour at 10-15° C.
  3. filtrationfiltered
  4. washwashed with 5 ml of methanol
  5. customThe product was dried in vacuum at 25-30° C. for 5 hours
  6. customby drying at 30-35° C. for 36 hours

Sources & evidence

ORD record
ord-a8767b68cdd44292a5407588722f3366
Source dataset
uspto-grants-2013_01
Patent number
US08349863B2

Linked notes

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