Ethanol → Raloxifene

HRID 1649611Notes

Reaction equation

HRID 1649611 reaction equation
Cl.C([O:10][C:11]1[CH:12]=[CH:13][C:14]2[C:18]([C:19](=[O:35])[C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][N:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)=[CH:22][CH:21]=3)=[C:17]([C:36]3[CH:41]=[CH:40][C:39]([O:42]C(=O)C4C=CC=CC=4)=[CH:38][CH:37]=3)[S:16][C:15]=2[CH:51]=1)(=O)C1C=CC=CC=1.C(O)C.CS(O)(=O)=O>O>[OH:10][C:11]1[CH:12]=[CH:13][C:14]2[C:18]([C:19](=[O:35])[C:20]3[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH2:28][N:29]4[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]4)=[CH:24][CH:25]=3)=[C:17]([C:36]3[CH:37]=[CH:38][C:39]([OH:42])=[CH:40][CH:41]=3)[S:16][C:15]=2[CH:51]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6395Methanesulfonic AcidHCID 1317128706-Benzoyloxy-2-(4-benzoyloxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene, hydrochloride

Product 1

HCID 5035Raloxifene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

The crude product of Example 2 above, 6-benzoyloxy-2-(4-benzoyloxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene, hydrochloride, was combined with 400 ml. of ethanol, 400 ml. of water and 55 ml. of methanesulfonic acid. The mixture was stirred on the steam bath for 72 hours, and was then evaporated down to an oil which was diluted to about 6 liters with water. The aqueous solution was washed twice with 1 liter portions of diethyl ether, and was then thoroughly degassed under vacuum, cooled to about 20° C., and made basic with aqueous ammonia to pH 8.4. The product which precipitated was collected by filtration and vacuum dried, and was then recrystallized from about 80 ml. of acetone. The product was vacuum dried at 40° C. to obtain 18.1 g. of crystals which was found by nmr, mass spectrum, infrared and ultraviolet analysis to be substantially identical to the product of Example 3.

Workup

  1. customwas then evaporated down to an oil which
  2. additionwas diluted to about 6 liters with water
  3. washThe aqueous solution was washed twice with 1 liter portions of diethyl ether
  4. customwas then thoroughly degassed under vacuum
  5. customThe product which precipitated
  6. filtrationwas collected by filtration and vacuum
  7. customdried
  8. customwas then recrystallized from about 80 ml
  9. customdried at 40° C.
  10. customto obtain 18.1 g

Sources & evidence

ORD record
ord-904ff4819a2c420882c2f4f5b0323720
Source dataset
uspto-grants-1983_11
Patent number
US04418068

Reaction notes

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