1-Phenylpiperazine → HCID 12941113, compound

HRID 1277601Notes

Reaction equation

HRID 1277601 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)=[O:8].[C:17]1([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C>C(O)C>[OH:16][C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:7](=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:26]2[CH2:27][CH2:28][N:23]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:24][CH2:25]2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 70961-PhenylpiperazineHCID 8471TriethylamineHCID 12941115HCID 12941115, compound

Product 1

HCID 12941113HCID 12941113, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 45.7 g (0.16 mol) of 6-bromo-N-(4-hydroxyphenyl)hexanamide, 26.0 g (0.16 mol) of 1-phenylpiperazine and 22.4 ml (16.3 g, 0.16 mol) of triethylamine in 400 ml of ethanol was heated under reflux overnight and then concentrated under vacuum. The residue was mixed with sodium bicarbonate solution and trichloromethane. The resulting suspension was filtered. The solid was recrystallized from ethanol-water and then from acetonitrile to give the end product as tan crystals, mp 157°-159°.

Workup

  1. temperatureunder reflux overnight
  2. concentrationconcentrated under vacuum
  3. additionThe residue was mixed with sodium bicarbonate solution and trichloromethane
  4. filtrationThe resulting suspension was filtered
  5. customThe solid was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-5513dc8e430d4fe6b0c6b80dd9e42749
Source dataset
uspto-grants-1981_07
Patent number
US04278608

Reaction notes

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