1-Phenylpiperazine → HCID 12941113, compound

HRID 1659468Notes

Reaction equation

HRID 1659468 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-c2bb8ea28bcf4ee9aaf2cdf6c2a6b9b1
Source dataset
uspto-grants-1981_12
Patent number
US04304721

Reaction notes

Loading…