Benzene → N-{4-[2-(1H-Indol-3-yl)ethyl]piperazin-1-yl}-N'-phenylurea

HRID 2398301Notes

Reaction equation

HRID 2398301 reaction equation
[NH2:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][CH:11]=2)[CH2:4][CH2:3]1.[C:19]1([N:25]=[C:26]=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1C=CC=CC=1>CCOCC>[NH:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([CH2:9][CH2:8][N:5]2[CH2:6][CH2:7][N:2]([NH:1][C:26]([NH:25][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:27])[CH2:3][CH2:4]2)=[CH:11]1

Participants

5

Reactant 3

HCID 241BenzeneHCID 7672Phenyl isocyanateHCID 12392200HCID 12392200, compound

Product 1

HCID 12464884N-{4-[2-(1H-Indol-3-yl)ethyl]piperazin-1-yl}-N'-phenylurea

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A stirred solution of 6.13 g of 3-[2-(4-aminopiperazin-1-yl)ethyl]indole and 3.53 g of phenylisocyanate in 100 ml. of dry benzene is refluxed for 6 hours and then allowed to stand at ambient temperature overnight. Ether is added slowly to promote crystallization. The solid product is filtered, washed with ether and dried. The solid is recrystallized twice from a dimethylformamide water mixture to give crystals m.p. 168°-171° C. of 1-[1-(indol-3-ylethyl)piperazin-4-yl]-3-phenylurea.

Workup

  1. customcrystallization
  2. filtrationThe solid product is filtered
  3. washwashed with ether
  4. customdried
  5. customThe solid is recrystallized twice from a dimethylformamide water mixture

Sources & evidence

ORD record
ord-1091fe74057547689aaad3f9ee05d6f0
Source dataset
uspto-grants-1977_05
Patent number
US04024258

Reaction notes

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