Ethanol → 6-Hydroxy-2-(4-hydroxyphenyl)-3-(4-(2-piperidinoethoxy)-benzoyl]benzo[b]thiophene Hydrochloride 1,2-Dichloroethane

HRID 1007856

Reaction equation

HRID 1007856 reaction equation
[ClH:1].C[O:3][C:4]1[CH:5]=[CH:6][C:7]2[C:11]([C:12](=[O:28])[C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)=[CH:15][CH:14]=3)=[C:10]([C:29]3[CH:34]=[CH:33][C:32]([O:35]C)=[CH:31][CH:30]=3)[S:9][C:8]=2[CH:37]=1.B(Cl)(Cl)[Cl:39].C(O)C.CO>ClCCCl>[Cl:1][CH2:8][CH2:37][Cl:39].[ClH:39].[OH:3][C:4]1[CH:5]=[CH:6][C:7]2[C:11]([C:12](=[O:28])[C:13]3[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][N:22]4[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]4)=[CH:17][CH:18]=3)=[C:10]([C:29]3[CH:30]=[CH:31][C:32]([OH:35])=[CH:33][CH:34]=3)[S:9][C:8]=2[CH:37]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 887MethanolHCID 25135Boron TrichlorideHCID 45260096Raloxifene Bismethyl Ether (hydrochloride)

Product 1

HCID 99168796-Hydroxy-2-(4-hydroxyphenyl)-3-(4-(2-piperidinoethoxy)-benzoyl]benzo[b]thiophene Hydrochloride 1,2-Dichloroethane

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
35 °C

Procedure

A solution of 6-methoxy-2-(4-methoxyphenyl)-3-(4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene hydrochloride (2.0 g) in 1,2-dichloroethane (20 mL) was treated with boron trichloride (2.0 mL). The resulting mixture was stirred at 35° C. for about 18 hours. A mixture of ethanol and methanol (10 mL, 95:5, 3A) was treated with the reaction mixture from above, causing the alcoholic mixture to reflux. Upon complete addition, the resulting crystalline slurry was stirred at 25° C. After one hour, the crystalline product was filtered, washed with cold ethanol (10 mL), and dried at 40° C. in vacuo to give 1.78 g of the title compound. The X-ray powder diffraction pattern is identical to that reported in Table 1.

Workup

  1. additionwas treated with the reaction mixture from above,
  2. temperatureto reflux
  3. additionUpon complete addition
  4. stirringthe resulting crystalline slurry was stirred at 25° C
  5. waitAfter one hour
  6. filtrationthe crystalline product was filtered
  7. washwashed with cold ethanol (10 mL)
  8. customdried at 40° C. in vacuo

Sources & evidence

ORD record
ord-86a2d21a65fc4037bd7b088758a92bb1
Source dataset
uspto-grants-2004_09
Patent number
US06797719B2

Linked notes

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