Acetone → Bazedoxifene Acetate

HRID 1503325Notes

Reaction equation

HRID 1503325 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.C[C:37]([CH3:39])=[O:38]>>[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.[CH3:39][C:37]([OH:17])=[O:38]

Participants

3

Reactant 2

HCID 180AcetoneHCID 154257Bazedoxifene

Product 1

HCID 154256Bazedoxifene Acetate

Conditions

Temperature
50 °C

Procedure

Bazedoxifene free base (700 mg) and acetone (8 mL) are mixed and stirred at 45-55° C. to make a clear solution. The solution is filtered followed by addition of seed crystals of bazedoxifene acetate (20 mg) and drop-wise addition of a mixture of acetic acid (0.1 mL) in acetone (1 mL) at room temperature. To the mixture, heptane (40 mL) is added over a period of 15-30 minutes and mixture is stirred for another 30 minutes. The solid so obtained is collected by filtration, washed with heptane (5 mL), and dried by suction. The obtained wet solid is then further dried under vacuum at below 70° C. for about 6-8 hours to afford 850 mg of crystalline bazedoxifene acetate Form D.

Workup

  1. filtrationThe solution is filtered
  2. additionfollowed by addition of seed crystals of bazedoxifene acetate (20 mg)
  3. additionaddition of a mixture of acetic acid (0.1 mL) in acetone (1 mL) at room temperature
  4. additionTo the mixture, heptane (40 mL) is added over a period of 15-30 minutes
  5. stirringmixture is stirred for another 30 minutes
  6. customThe solid so obtained
  7. filtrationis collected by filtration
  8. washwashed with heptane (5 mL)
  9. customdried by suction
  10. customThe obtained wet solid is then further dried under vacuum at below 70° C. for about 6-8 hours

Sources & evidence

ORD record
ord-5ca1e6558ca54a48b54086cd12c62c73
Source dataset
uspto-grants-2015_12
Patent number
US09212172B2

Reaction notes

Loading…