Methanol → HCID 15294981, compound

HRID 374823Notes

Reaction equation

HRID 374823 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][CH:30]([OH:33])[CH2:29][CH2:28]3)[S:7][C:6]=2[CH:34]=1.[C:35](OC(=O)C)(=[O:37])[CH3:36].N1[CH:47]=[CH:46]C=CC=1.C(Cl)(Cl)Cl.C[OH:53]>>[C:35]([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[CH2:28][CH2:29][CH:30]([O:33][C:46](=[O:53])[CH3:47])[CH2:31][CH2:32]3)[S:7][C:6]=2[CH:34]=1)(=[O:37])[CH3:36]

Participants

6

Reactant 5

HCID 887MethanolHCID 1049PyridineHCID 6212ChloroformHCID 7918Acetic AnhydrideHCID 9982581HCID 9982581, compound

Product 1

HCID 15294981HCID 15294981, compound

Procedure

A mixture of 10 mg of (6-hydroxy-2-(4-hydroxycyclohexyl)benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone, 0.5 mL of acetic anhydride, and 0.5 mL of pyridine is agitated for 18 hours at room temperature. Ice is added to the reaction mixture, and the system is agitated for 30 minutes, after which the organic layer is extracted with ethyl acetate, washed with water and a saturated aqueous solution of sodium hydrogencarbonate, 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 5 mg of [6-acetoxy-2-(4-acetoxycyclohexyl)benzo[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 30 minutes
  3. extractionafter which the organic layer is extracted with ethyl acetate
  4. washwashed with water
  5. dry with materiala saturated aqueous solution of sodium hydrogencarbonate, and dried with anhydrous magnesium sulfate
  6. distillationThe solvent is distilled off
  7. customthe crude product thus obtained

Sources & evidence

ORD record
ord-96e0934c5c2d4704a85bd5a3808f2e23
Source dataset
uspto-grants-1996_01
Patent number
US05482950

Reaction notes

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