Sodium Hydroxide → HCID 20098353, compound

HRID 1165219Notes

Reaction equation

HRID 1165219 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[C:12]2[CH:13]=[CH:14][NH:15][C:16]=2[CH:17]=[CH:18][CH:19]=1)=[O:10].[OH-].[Na+].[N:22]1([CH2:28][CH2:29]Cl)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>C1C=CC=CC=1.C(#N)C>[N:22]1([CH2:28][CH2:29][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[NH:8][C:9]([C:11]2[C:12]3[CH:13]=[CH:14][NH:15][C:16]=3[CH:17]=[CH:18][CH:19]=2)=[O:10])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 748271-(2-Chloroethyl)piperidineHCID 13787417HCID 13787417, compound

Product 1

HCID 20098353HCID 20098353, compoundYield 83.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6342AcetonitrileSolvent

Procedure

3 g of N-(2-hydroxyphenyl)-1H-indol-4-carboxamide in 50 ml of benzene, 25 ml of acetonitrile and 50 ml of a 5N aqueous solution of sodium hydroxide were heated to 60° C. for 3 hours with stirring under an inert atmosphere with 0.4 g of 2-tetrabutylammonium hydrogenosulfate and 2.2 g of 2-piperidino-1-chloroethane. After cooling, decanting, extracting with ethyl acetate and purifying by chromatography over silica (eluent: ethyl acetate-triethylamine, 9-1), 3.6 g of N-[2-[2-(1-piperidinyl)ethoxy]phenyl]-1H-indol-4-carboxamide were obtained.

Workup

  1. temperatureAfter cooling
  2. customdecanting
  3. extractionextracting with ethyl acetate
  4. custompurifying by chromatography over silica (eluent: ethyl acetate-triethylamine, 9-1)

Sources & evidence

ORD record
ord-a79bbba95c704145a0870a758fdbe93d
Source dataset
uspto-grants-1990_03
Patent number
US04908367

Reaction notes

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