Pyridine → HCID 22666403, compound

HRID 1007921Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][N:15]([CH3:19])[CH2:16][CH2:17][OH:18])[CH:8]=[CH:9][C:2]1=2.N1C=CC=CC=1.[C:26](OC(=O)C)(=[O:28])[CH3:27].C(=O)([O-])O.[Na+]>C(Cl)Cl.O>[C:26]([O:18][CH2:17][CH2:16][N:15]([CH2:14][CH2:13][O:12][CH2:11][CH2:10][C:7]1[CH:8]=[CH:9][C:2]2[S:1][CH:5]=[CH:4][C:3]=2[CH:6]=1)[CH3:19])(=[O:28])[CH3:27]

Participants

Conditions

Temperature: 5 °C

Procedure

In 10 mL of methylene chloride is dissolved 1.00 g of 2-{[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl]-(methyl)amino}-1-ethanol. The solution thus obtained is cooled to 5° C., to which are added 0.32 mL of pyridine, 0.37 mL of acetic anhydride and 0.04 g of N,N-dimethylaminopyridine. The mixture is stirred at ambient temperature for 30 minutes. Water is added to the mixture, pH is adjusted to 7.5 with saturated aqueous solution of sodium hydrogen carbonate, and the organic layer is separated. The organic layer is washed with saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, the solvent is distilled off under reduced pressure, and the residue is purified by column chromatography (eluent: chloroform:methanol=100:1 to 50:1) to obtain 1.14 g of 2-{[2-(2-benzo[b]-thiophen-5-ylethoxy)-ethyl](methyl)amino}ethyl acetate as an oily product.

Workup

customThe solution thus obtained
customthe organic layer is separated
washThe organic layer is washed with saturated aqueous solution of sodium chloride
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent is distilled off under reduced pressure
customthe residue is purified by column chromatography (eluent: chloroform:methanol=100:1 to 50:1)

Sources & evidence

ORD record: ord-5e299a20f662461e86f218b447f88fcd
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06797726B1

Reaction notes

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