Acetone → Bazedoxifene Acetate

HRID 1503324Notes

Reaction equation

HRID 1503324 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
55 °C

Procedure

Bazedoxifene free base (500 mg) and acetone (8 mL) are mixed and stirred at 50-60° C. to make a clear solution. The solution is filtered followed by addition of seed crystals of bazedoxifene acetate (10 mg) and drop-wise addition of acetic acid (0.12 mL). To the mixture, heptane (40 mL) is added over a period of 10 and mixture is stirred for another 10-15 minutes. The solid so obtained is collected by filtration, washed with heptane (10 mL), and dried by suction. The obtained wet solid is then further dried under vacuum at 65-70° C. for about 6-8 hours to afford 400 mg of crystalline bazedoxifene acetate Form D.

Workup

  1. filtrationThe solution is filtered
  2. additionfollowed by addition of seed crystals of bazedoxifene acetate (10 mg)
  3. additionaddition of acetic acid (0.12 mL)
  4. additionTo the mixture, heptane (40 mL) is added over a period of 10 and mixture
  5. stirringis stirred for another 10-15 minutes
  6. customThe solid so obtained
  7. filtrationis collected by filtration
  8. washwashed with heptane (10 mL)
  9. customdried by suction
  10. customThe obtained wet solid is then further dried under vacuum at 65-70° C. for about 6-8 hours

Sources & evidence

ORD record
ord-dbb3f734c11045efac170c13d99aa8a8
Source dataset
uspto-grants-2015_12
Patent number
US09212172B2

Reaction notes

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