Methanol → (6-Benzoyloxy-2-cyclohexylbenzo[b]thien-3-yl)[4-[2-(1-piperidinyl)ethoxy]phenyl]methanone

HRID 374822Notes

Reaction equation

HRID 374822 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][N:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:14][CH:13]=3)=[O:11])=[C:8]([CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[S:7][C:6]=2[CH:33]=1.[C:34](Cl)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(Cl)(Cl)Cl.CO>N1C=CC=CC=1>[C:34]([O:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([C:10]([C:12]3[CH:13]=[CH:14][C:15]([O:18][CH2:19][CH2:20][N:21]4[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]4)=[CH:16][CH:17]=3)=[O:11])=[C:8]([CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[S:7][C:6]=2[CH:33]=1)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6212ChloroformHCID 7412Benzoyl chlorideHCID 9825662Methanone, (2-cyclohexyl-6-hydroxybenzo(b)thien-3-yl)(4-(2-(1-piperidinyl)ethoxy)phenyl)-

Product 1

HCID 15294980(6-Benzoyloxy-2-cyclohexylbenzo[b]thien-3-yl)[4-[2-(1-piperidinyl)ethoxy]phenyl]methanone

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

27 mg of (6-hydroxy-2-cyclohexylbenzo[b]thien-3yl)[4[2-(1-piperidinyl)ethoxy]phenyl]methanone is dissolved in 1 mL of pyridine, 0.1 mL of benzoyl chloride is added, and this mixture is agitated for one hour at room temperature. Ice is added to the reaction mixture, and the system is agitated for one hour. The organic layer is extracted with ethyl acetate and dried with anhydrous magnesium sulfate. The solvent is distilled off, and the crude product thus obtained is refined by TLC (developing solvent was chloroform:methanol=9:1), which gives 37 mg of (6-benzoyloxy-2-cyclohexylbenzo[b]thien-3-yl)[4-[2-(1-piperidinyl)ethoxy]phenyl]methanone.

Workup

  1. additionIce is added to the reaction mixture
  2. stirringthe system is agitated for one hour
  3. extractionThe organic layer is extracted with ethyl acetate
  4. dry with materialdried with anhydrous magnesium sulfate
  5. distillationThe solvent is distilled off
  6. customthe crude product thus obtained

Sources & evidence

ORD record
ord-c5567fc282cf46cfb4f944cff8ea299c
Source dataset
uspto-grants-1996_01
Patent number
US05482950

Reaction notes

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