Bazedoxifene HCl → Bazedoxifene

HRID 1503314Notes

Reaction equation

HRID 1503314 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 86.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
65 °C

Procedure

Bazedoxifene hydrochloride (1 g) and dimethylsulfoxide (10 mL) are mixed and heated to 60-70° C. to produce a clear solution, followed by filtration. To the filtrate, toluene (50 mL), morpholine (1 mL), and water (30 mL) are added and the mixture is stirred at room temperature for 12-24 hours. The solid so formed is collected by filtration, washed with toluene (5 mL), water (5 mL) and dried under vacuum below 80° C. for about 7 hours to afford 800 mg of crystalline bazedoxifene free base Form A.

Workup

  1. customto produce a clear solution
  2. filtrationfollowed by filtration
  3. additionTo the filtrate, toluene (50 mL), morpholine (1 mL), and water (30 mL) are added
  4. customThe solid so formed
  5. filtrationis collected by filtration
  6. washwashed with toluene (5 mL), water (5 mL)
  7. customdried under vacuum below 80° C. for about 7 hours

Sources & evidence

ORD record
ord-5fc5dc11282f4d87926919d2be118e07
Source dataset
uspto-grants-2015_12
Patent number
US09212172B2

Reaction notes

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