Bazedoxifene Acetate → Bazedoxifene

HRID 1503311

Reaction equation

HRID 1503311 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 154257BazedoxifeneYield 75.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
72.5 °C

Procedure

Bazedoxifene acetate (15 g) and dimethylformamide (75 mL) are mixed and heated to 70-75° C. to produce a clear solution, followed by filtration to make it particle free. To the filtrate, toluene (1000 mL), morpholine (1 mL), and water (500 mL) are added and the mixture is cooled to 25-30° C. and stirred overnight. The solid that forms is collected by filtration, washed with toluene (20 mL), and dried under vacuum at 70° C. for 5 hours to afford 10 g of crystalline bazedoxifene free base Form A.

Workup

  1. customto produce a clear solution
  2. filtrationfollowed by filtration
  3. additionTo the filtrate, toluene (1000 mL), morpholine (1 mL), and water (500 mL) are added
  4. temperaturethe mixture is cooled to 25-30° C.
  5. filtrationThe solid that forms is collected by filtration
  6. washwashed with toluene (20 mL)
  7. customdried under vacuum at 70° C. for 5 hours

Sources & evidence

ORD record
ord-26db185c049d42e98fd7a3967d07ba63
Source dataset
uspto-grants-2015_12
Patent number
US09212172B2

Linked notes

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