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Potassium Carbonate → 1-[2-(Pyridin-4-yloxymethyl)phenyl]piperazine

HRID 907579
Notes
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Reaction equation

HRID 907579 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH2:13][OH:14])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl.Cl[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1.[OH-].[K+].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[N:20]1[CH:21]=[CH:22][C:17]([O:14][CH2:13][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)=[CH:18][CH:19]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 818524-Chloropyridine hydrochlorideHCID 220780362-(1-Piperazinyl)benzyl alcohol

Product 1

HCID 673880841-[2-(Pyridin-4-yloxymethyl)phenyl]piperazine

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Conditions

Temperature
120 °C

Procedure

(2-piperazin-1-yl-phenyl)-methanol (200 mg, 1.04 mmol) was added to a suspension of 4-chloropyridine hydrochloride (225 mg, 1.50 mmol), tris[2-(2-methoxy)ethyl]amine (32 μL, 0.10 mmol), powdered potassium hydroxide (225 mg, 4.01 mmol) and potassium carbonate (275 mg, 1.99 mmol) in 10 mL of toluene. The reaction mixture was heated to 120° C. overnight. The reaction mixture was concentrated and the residue was purified by reverse phase HPLC. The material was still less than 50% pure, but was used in the next step without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by reverse phase HPLC
  3. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-63efc5a767ff47479a445c16e8636545
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08013156B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes