Bazedoxifene HCl → Bazedoxifene

HRID 1503316Notes

Reaction equation

HRID 1503316 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:5]=2[N:4]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][N:22]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:15][CH:14]=2)[C:3]=1[C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1.Cl>CS(C)=O>[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:5]=2[N:4]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][N:22]3[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)=[CH:17][CH:18]=2)[C:3]=1[C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1

Participants

3

Reactant 1

HCID 9936012Bazedoxifene HCl

Product 1

HCID 154257BazedoxifeneYield 91.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
65 °C

Procedure

Bazedoxifene hydrochloride (2 g) and dimethylsulfoxide (16 mL) are mixed and heated to 60-70° C. to produce a clear solution, followed by cooling to room temperature and filtration to make it particle free. To the filtrate, toluene (100 mL), aqueous sodium carbonate solution (10%, 5 mL) and water (50 mL) are added and the mixture is stirred at room temperature for solid formation. The solid so formed is collected by filtration, washed with toluene (5 mL), water (5 mL) and dried under vacuum below 80° C. to afford 1.7 g of crystalline bazedoxifene free base Form A.

Workup

  1. customto produce a clear solution
  2. temperatureby cooling to room temperature
  3. filtrationfiltration
  4. additionTo the filtrate, toluene (100 mL), aqueous sodium carbonate solution (10%, 5 mL) and water (50 mL) are added
  5. customThe solid so formed
  6. filtrationis collected by filtration
  7. washwashed with toluene (5 mL), water (5 mL)
  8. customdried under vacuum below 80° C.

Sources & evidence

ORD record
ord-a496b43fff4b4b50816c84afab6fad55
Source dataset
uspto-grants-2015_12
Patent number
US09212172B2

Reaction notes

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