Triethylamine → 4-(4-(4-Pyridyl)piperazin-1-yl)phenol

HRID 427452Notes

Reaction equation

HRID 427452 reaction equation
Cl.Cl[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.C[O:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[CH:13][CH:12]=1.C(N(CC)CC)C>C(O)C.O>[OH:10][C:11]1[CH:12]=[CH:13][C:14]([N:17]2[CH2:22][CH2:21][N:20]([C:3]3[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=3)[CH2:19][CH2:18]2)=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 818524-Chloropyridine hydrochlorideHCID 2697221-(4-Methoxyphenyl)piperazine

Product 1

HCID 149869034-(4-(4-Pyridyl)piperazin-1-yl)phenolYield 9.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A solution of 4-chloropyridine HCl (450 mg) and 1-(4-methoxyphenyl)-piperazine (226 mg) in ethanol (20 ml) and water (2 ml) containing triethylamine (0.5 ml) was heated under reflux for 18 hours. The solution was evaporated, water (50 ml) added and the solution taken to pH 8 by addition of solid potassium carbonate to give a precipitate which was filtered, washed with water and dried. The solid (33 mg) was stirred in concentrated aqueous hydrogen bromide (2 ml) at 140° C. for 8 hours, poured into cold water (2 ml) and taken to pH 7 with aqueous ammonia (1.3 ml) to give a solid which was filtered, washed with water and dried to give 1-(4-hydroxyphenyl)-4-(4-pyridyl)piperazine (28 mg), m.p. 288-290° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. customThe solution was evaporated
  4. additionwater (50 ml) added
  5. additionthe solution taken to pH 8 by addition of solid potassium carbonate
  6. customto give a precipitate which
  7. filtrationwas filtered
  8. washwashed with water
  9. customdried
  10. additionpoured into cold water (2 ml)
  11. customto give a solid which
  12. filtrationwas filtered
  13. washwashed with water
  14. customdried

Sources & evidence

ORD record
ord-7b30be74c96e4da3ab0b26efde51b5f3
Source dataset
uspto-grants-2001_11
Patent number
US06313127B1

Reaction notes

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