Bazedoxifene Acetate → Bazedoxifene

HRID 1503312

Reaction equation

HRID 1503312 reaction equation
[CH3:1][C:2]1[C:3]2[CH:4]=[C:5]([OH:35])[CH:6]=[CH:7][C:8]=2[N:9]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][CH2:26][CH2:27][N:28]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[CH:23][CH:24]=2)[C:10]=1[C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1.CC(O)=O>CN(C)C=O>[CH3:1][C:2]1[C:3]2[CH:4]=[C:5]([OH:35])[CH:6]=[CH:7][C:8]=2[N:9]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]3)=[CH:21][CH:20]=2)[C:10]=1[C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1

Participants

3

Reactant 1

HCID 154256Bazedoxifene Acetate

Product 1

HCID 154257Bazedoxifene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
72.5 °C

Procedure

Bazedoxifene acetate (2 g) and dimethylformamide (10 mL) are mixed and heated to 70-75° C. to produce a clear solution, followed by filtration. To the filtrate, toluene (400 mL), morpholine (1 mL), and water (100 mL) are added and the mixture is cooled to 0-10° C. and stirred overnight. The solid that forms is collected by filtration, washed with toluene (20 mL), and dried under vacuum below 80° C. for about 5 hours to afford crystalline bazedoxifene free base Form A (HPLC purity 99.2%, moisture content=0.32%).

Workup

  1. customto produce a clear solution
  2. filtrationfollowed by filtration
  3. additionTo the filtrate, toluene (400 mL), morpholine (1 mL), and water (100 mL) are added
  4. temperaturethe mixture is cooled to 0-10° C.
  5. filtrationThe solid that forms is collected by filtration
  6. washwashed with toluene (20 mL)
  7. customdried under vacuum below 80° C. for about 5 hours

Sources & evidence

ORD record
ord-afb1ac55da2e44bbae276455bdd81ad3
Source dataset
uspto-grants-2015_12
Patent number
US09212172B2

Linked notes

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