Sodium Carbonate → HCID 20068626, compound

HRID 981895Notes

Reaction equation

HRID 981895 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[N:4][C:3]=1[N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.[OH-].[Na+].Br[CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C([O-])([O-])=O.[Na+].[Na+]>O>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][CH2:18][CH2:17][N:11]1[CH2:12][CH2:13][N:8]([C:3]2[N:4]=[CH:5][CH:6]=[CH:7][N:2]=2)[CH2:9][CH2:10]1)[CH3:24]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 76300Ethyl 4-bromobutyrateHCID 28184571-(2-Pyrimidyl)piperazine hydrochloride

Product 1

HCID 20068626HCID 20068626, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.2 equivalents of 1-(2-pyrimidinyl)piperazine hydrochloride was dissolved in water and the solution made strongly basic (pH 12-14) with 10% NaOH. The 2-phase mixture (the product is a yellow oil) was extracted three times with methyl isobutyl ketone (MIBK). The MIBK solution resulting was placed in a single neck round bottom flask fitted with magnetic stirrer, condenser and nitrogen atmosphere, and a Dean-Stark trap. To this solution was added 1 equivalent of ethyl 4-bromobutyrate, 1.1 equivalent of Na2CO3 and a catalytic quantity of KI. The resulting mixture was then refluxed for 4 hours and then cooled to room temperature. Inorganic solids were filtered off and the filtrate was condensed to give the title compound yellow oil. Yield 75%.

Workup

  1. extractionwas extracted three times with methyl isobutyl ketone (MIBK)
  2. customThe MIBK solution resulting
  3. customwas placed in a single neck round bottom flask
  4. customfitted with magnetic stirrer, condenser
  5. temperatureThe resulting mixture was then refluxed for 4 hours
  6. filtrationInorganic solids were filtered off
  7. customcondensed

Sources & evidence

ORD record
ord-38cd55b9c721489fb7f60ad27f429823
Source dataset
uspto-grants-1991_02
Patent number
US04994455

Reaction notes

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