Ethanesulfonyl chloride → HCID 57499607, compound

HRID 655669Notes

Reaction equation

HRID 655669 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([N:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][O:19][C:20]4[C:25]([CH3:26])=[CH:24][C:23]([NH2:27])=[CH:22][C:21]=4[O:28][CH3:29])[CH2:12][CH2:11]3)=[CH:7][CH:8]=[CH:9][C:2]1=2.C(N(C(C)C)C(C)C)C.[CH2:39]([S:41]([Cl:44])(=[O:43])=[O:42])[CH3:40].[OH-].[Na+]>ClCCl.C(O)C>[ClH:44].[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([N:10]3[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][CH2:18][O:19][C:20]4[C:25]([CH3:26])=[CH:24][C:23]([NH:27][S:41]([CH2:39][CH3:40])(=[O:43])=[O:42])=[CH:22][C:21]=4[O:28][CH3:29])[CH2:14][CH2:15]3)=[CH:7][CH:8]=[CH:9][C:2]1=2

Participants

7

Reactant 4

HCID 11667Ethanesulfonyl chloride2×HCID 14798Sodium HydroxideHCID 81531Diisopropylethylamine2×HCID 16044905HCID 16044905, compound

Product 1

HCID 57499607HCID 57499607, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A dichloromethane solution (4 ml) of 4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3-methoxy-5-methylphenylamine (0.2 g, 0.49 mmol) was cooled on ice. To this, N-ethyldiisopropylamine (0.15 ml, 0.87 mmol) and ethane sulfonylchloride (0.07 ml, 0.73 mmol) were added and the mixture was stirred at room temperature for one hour. Further, N-ethyldiisopropylamine (0.15 ml, 0.87 mmol) and ethane sulfonylchloride (0.07 ml, 0.73 mmol) were added and the mixture was stirred at room temperature for 19 hours. To this, an aqueous 6N-sodium hydroxide solution (0.5 ml) and ethanol (2 ml) were added and the mixture was stirred at room temperature overnight. Dichloromethane was added to the reaction solution, which was then washed with water. The organic layer was dried over anhydrous magnesium sulfate and thereafter concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (n-hexane:ethyl acetate=2:1→0:1). The purified product was concentrated under reduced pressure. 4N-hydrochloride/ethyl acetate solution was added to the residue. The crystal generated was filtrated and dried to obtain ethanesulfonic acid {4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3-methoxy-5-methyl-phenyl}amide hydrochloride (222 mg, 85% yield) as white powder.

Workup

  1. stirringthe mixture was stirred at room temperature for 19 hours
  2. stirringthe mixture was stirred at room temperature overnight
  3. washwas then washed with water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by basic silica gel column chromatography (n-hexane:ethyl acetate=2:1→0:1)
  7. concentrationThe purified product was concentrated under reduced pressure
  8. addition4N-hydrochloride/ethyl acetate solution was added to the residue
  9. filtrationThe crystal generated was filtrated
  10. customdried

Sources & evidence

ORD record
ord-622542c3b6834feeb93fdbc7c993c089
Source dataset
uspto-grants-2011_12
Patent number
US08071600B2

Reaction notes

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