HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sodium Hydroxide → N-methyl-4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3-methoxy-5-methylaniline hydrochloride

HRID 655664
Notes
Print preview

Reaction equation

HRID 655664 reaction equation
[ClH:1].[Na].Cl.[S:4]1[CH:8]=[CH:7][C:6]2[C:9]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][O:22][C:23]4[C:28]([CH3:29])=[CH:27][C:26]([NH:30][CH:31]=O)=[CH:25][C:24]=4[O:33][CH3:34])[CH2:15][CH2:14]3)=[CH:10][CH:11]=[CH:12][C:5]1=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1.O>[ClH:1].[CH3:31][NH:30][C:26]1[CH:27]=[C:28]([CH3:29])[C:23]([O:22][CH2:21][CH2:20][CH2:19][N:16]2[CH2:17][CH2:18][N:13]([C:9]3[C:6]4[CH:7]=[CH:8][S:4][C:5]=4[CH:12]=[CH:11][CH:10]=3)[CH2:14][CH2:15]2)=[C:24]([O:33][CH3:34])[CH:25]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 23872008Sodium hydrochlorideHCID 574995784-[3-(4-Benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3-methoxy-5-methylphenyl formamide hydrochloride

Product 1

HCID 16044808N-methyl-4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3-methoxy-5-methylaniline hydrochloride

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A 6N aqueous sodium hydrochloride solution was added to N-(4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3-methoxy-5-methylphenyl formamide hydrochloride (0.23 g, 0.48 mmol) and the solution mixture was extracted with dichloromethane. The extraction solution with dichloromethane was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was dissolved in a tetrahydrofuran (THF) solution (5 ml) and lithium aluminum hydride (30 mg, 0.71 mmol) was added thereto under ice cooling and refluxed with heating for 15 minutes. The reaction solution was cooled on ice, and water (0.03 ml), 15% aqueous sodium hydroxide solution (0.03 ml), and water (0.09 ml) were added to the reaction mixture in this order and stirred. Insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (n-hexane:ethyl acetate=5:1→3:1) and concentrated under reduced pressure. A solution of 4N-hydrochloric acid/ethyl acetate was added to an ethyl acetate solution of the residue, and the insoluble matter precipitated was obtained by filtration to obtain N-methyl-4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3-methoxy-5-methylaniline hydrochloride (63 mg) as white powder.

Workup

  1. extractionthe solution mixture was extracted with dichloromethane
  2. dry with materialThe extraction solution with dichloromethane was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. additionwas added
  5. temperatureunder ice cooling and refluxed
  6. temperaturewith heating for 15 minutes
  7. additionwere added to the reaction mixture in this order
  8. customInsoluble matter was removed by filtration
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe obtained residue was purified by basic silica gel column chromatography (n-hexane:ethyl acetate=5:1→3:1)
  11. concentrationconcentrated under reduced pressure
  12. additionA solution of 4N-hydrochloric acid/ethyl acetate was added to an ethyl acetate solution of the residue
  13. customthe insoluble matter precipitated
  14. customwas obtained by filtration

Sources & evidence

ORD record
ord-cb9fed83f42442ccbbc382f15cc1a88d
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08071600B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes