1-Phenylpiperazine → HCID 12941114, compound

HRID 1065228Notes

Reaction equation

HRID 1065228 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)=[O:13].[C:22]1([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(O)C.ClCCl>[OH:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:12](=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:31]2[CH2:32][CH2:33][N:28]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:29][CH2:30]2)=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 70961-PhenylpiperazineHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 12941116HCID 12941116, compound

Product 1

HCID 12941114HCID 12941114, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 66.8 g (0.187 mol) of 11-bromo-N-(4-hydroxyphenyl)undecanamide, 30.3 g (0.187 mol) of 1-phenylpiperazine and 27.0 ml (19.6 g, 0.194 mol) of triethylamine in 600 ml of ethanol was heated under reflux overnight and then cooled. The resulting solid was shaken with sodium bicarbonate soluion and dichloromethane and the suspension was filtered. The solid was recrystallized from 95% ethanol to give the end product as colorless crystals, mp 160.5°-162.5° C.

Workup

  1. temperatureunder reflux overnight
  2. temperaturecooled
  3. filtrationthe suspension was filtered
  4. customThe solid was recrystallized from 95% ethanol

Sources & evidence

ORD record
ord-950395df42b5401ca20cf5d0f4bcb70f
Source dataset
uspto-grants-1982_05
Patent number
US04329289

Reaction notes

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