Triethylamine → [6-(n-Hexylsulfonoyl)-2-[4-(n-hexylsulfonoyl)phenyl]benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]-phenyl] methanone

HRID 325154

Reaction equation

HRID 325154 reaction equation
Cl.O[C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([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)=[O:12])=[C:9]([C:28]3[CH:33]=[CH:32][C:31](O)=[CH:30][CH:29]=3)[S:8][C:7]=2[CH:35]=1.C(N([CH2:41][CH3:42])CC)C.[CH2:43]([S:49](Cl)(=[O:51])=[O:50])[CH2:44][CH2:45][CH2:46][CH2:47][CH3:48]>CN(C1C=CN=CC=1)C.O1CCCC1>[CH2:43]([S:49]([C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)=[CH:17][CH:18]=3)=[O:12])=[C:9]([C:28]3[CH:29]=[CH:30][C:31]([S:49]([CH2:43][CH2:44][CH2:45][CH2:46][CH2:41][CH3:42])(=[O:51])=[O:50])=[CH:32][CH:33]=3)[S:8][C:7]=2[CH:35]=1)(=[O:51])=[O:50])[CH2:44][CH2:45][CH2:46][CH2:47][CH3:48]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 54900Raloxifene HydrochlorideHCID 845041-Hexanesulfonyl chloride

Product 1

HCID 18357255[6-(n-Hexylsulfonoyl)-2-[4-(n-hexylsulfonoyl)phenyl]benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]-phenyl] methanone

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

In dry tetrahydrofuran (250 ml) 3 g (5.9 mmol) of [6-hydroxy-2-(4-hydroxyphenyl)-benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]-methanone hydrochloride was suspended and 10 mg of DMAP was added. Triethylamine (4 g, 40 mmol) was then added and the reaction mixture was stirred for 20 minutes at room temperature under a nitrogen blanket. n-Hexylsulfonyl chloride (3.6 g, 19.6 mmol) in 25 ml of tetrahydrofuran was slowly added to the reaction mixture. The reaction was allowed to proceed at room temperature and under nitrogen for 3 days. The reaction mixture was evaporated down in vacuo and resuspended in ethyl acetate and washed with water. The organic layer was dried by filtering it through anhydrous sodium sulfate and evaporated to a yellow oil. The oil was dissolved in chloroform and chromatographed (HPLC) on a silica gel column and eluted with a linear gradient starting with chloroform and ending with chloroform-methanol (19:1 v/v). The desired fractions were determined by thin layer chromatography, combined and evaporated down to afford 3.14 g of the title compound as a thick oil.

Workup

  1. waitto proceed at room temperature and under nitrogen for 3 days
  2. customThe reaction mixture was evaporated down in vacuo
  3. washwashed with water
  4. customThe organic layer was dried
  5. filtrationby filtering it through anhydrous sodium sulfate
  6. customevaporated to a yellow oil
  7. dissolutionThe oil was dissolved in chloroform
  8. customchromatographed (HPLC) on a silica gel column
  9. washeluted with a linear gradient
  10. customevaporated down

Sources & evidence

ORD record
ord-ceb22f74969c48fe8b37535171125830
Source dataset
uspto-grants-2001_04
Patent number
US06221838B1

Linked notes

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