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

Potassium Iodide → 1-Acetyl-5-[2-[2-(2-ethoxyphenoxy)ethylamino]propyl]indoline-7-carbonitrile

HRID 273853
Notes
Print preview

Reaction equation

HRID 273853 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:15][CH:16](Br)[CH3:17])=[CH:10][C:11]=2[C:13]#[N:14])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH2:19]([O:21][C:22]1[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=1[O:24][CH2:25][CH2:26][NH2:27])[CH3:20].[I-].[K+].C1OCCOCCOCCOCCOCCOC1>O1CCOCC1>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:15][CH:16]([NH:27][CH2:26][CH2:25][O:24][C:23]3[CH:28]=[CH:29][CH:30]=[CH:31][C:22]=3[O:21][CH2:19][CH3:20])[CH3:17])=[CH:10][C:11]=2[C:13]#[N:14])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 2855718-Crown-6HCID 53030422-(2-Ethoxyphenoxy)ethylamineHCID 200943711-Acetyl-5-(2-bromopropyl)indoline-7-carbonitrile

Product 1

HCID 200943411-Acetyl-5-[2-[2-(2-ethoxyphenoxy)ethylamino]propyl]indoline-7-carbonitrileYield 27.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1-acetyl-5-(2-bromopropyl)indoline-7-carbonitrile (300 mg) and 2-(2-ethoxyphenoxy)ethylamine (391 mg) in dioxane (4 ml) were added potassium iodide (17 mg) and 18-crown-6 (26 mg), and the mixture was reacted in a sealed tube at 180° C. for 18 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel using a mixture of methylene chloride and methanol (40/1) as eluent to give 111 mg of 1-acetyl-5-[2-[2-(2-ethoxyphenoxy)ethylamino] propyl]indoline-7-carbonitrile as an oil.

Workup

  1. customthe mixture was reacted in a sealed tube at 180° C. for 18 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by flash column chromatography on silica gel using
  4. additiona mixture of methylene chloride and methanol (40/1) as eluent

Sources & evidence

ORD record
ord-e53de1fde71a4a9685917c3b4ede803c
Source dataset
uspto-grants-1995_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05387603

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes