Ethanol → 4-(4-Chloro-2-phenylpyrimidin-6-yl)-1-piperazineethanol

HRID 1578972Notes

Reaction equation

HRID 1578972 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.C(O)C.[Cl:13][C:14]1[CH:19]=[C:18](Cl)[N:17]=[C:16]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:15]=1>O>[Cl:13][C:14]1[CH:19]=[C:18]([N:7]2[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][OH:1])[CH2:5][CH2:6]2)[N:17]=[C:16]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:15]=1

Participants

5

Reactant 3

HCID 702Ethanol2×HCID 76771-(2-Hydroxyethyl)piperazineHCID 77338Fenclorim

Product 1

HCID 215573704-(4-Chloro-2-phenylpyrimidin-6-yl)-1-piperazineethanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-hydroxyethylpiperazine (7.81 g.) diluted with 20 ml. of absolute ethanol is added to a slurry obtained by adding 6.75 g. of 4,6-dichloro-2-phenylpyrimidine to 25 ml. of absolute ethanol. The resulting mixture is refluxed for fifteen minutes, then poured into 850 ml. of water. A gummy material which separates solidifies on standing overnight. The crude product weighs 7.8 g. which is recrystallized from n-heptane to afford 4-(4-chloro-2-phenylpyrimidin-6-yl)-1-piperazineethanol, m.p. 103°-105°C.

Workup

  1. customobtained
  2. additionby adding 6.75 g
  3. temperatureThe resulting mixture is refluxed for fifteen minutes
  4. additionpoured into 850 ml
  5. customwhich is recrystallized from n-heptane

Sources & evidence

ORD record
ord-c025e91e4f0947c5a1a9d0dd6dee8eaa
Source dataset
uspto-grants-1976_02
Patent number
US03940395

Reaction notes

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