1-Butanol → HCID 9279521, compound

HRID 1995080Notes

Reaction equation

HRID 1995080 reaction equation
Br.Br.[N:3]1([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.Cl[C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1.C(=O)([O-])[O-].[K+].[K+].C(O)CCC>O.O(C(C)C)C(C)C>[N:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:25]=[CH:26][C:17]=1[N:6]1[CH2:5][CH2:4][N:3]([C:9]2[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=2)[CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 2631-ButanolHCID 11430Potassium CarbonateHCID 119282-ChloroquinolineHCID 2723591p-(1-Piperazinyl)phenol dihydrobromide

Product 1

HCID 9279521HCID 9279521, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7914Diisopropyl EtherSolvent

Procedure

A mixture of 10.2 parts of 4-(1-piperazinyl)phenol dihydrobromide, 5.7 parts of 2-chloroquinoline, 6.3 parts of potassium carbonate and 80 parts of 1-butanol is stirred and refluxed overnight. The reaction mixture is diluted with water and 2,2'-oxybispropane is added; the product is crystallized. It is filtered off and recrystallized from 4-methyl-2-pentanone, yielding 6.4 parts (70%) of 4-[4-(2-quinolinyl)-1-piperazinyl]phenol; mp. 198.1° C.

Workup

  1. temperaturerefluxed overnight
  2. additionis added
  3. customthe product is crystallized
  4. filtrationIt is filtered off
  5. customrecrystallized from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-4ceec86e589c4a0fa995d303b306f8c7
Source dataset
uspto-grants-1983_09
Patent number
US04402957

Reaction notes

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