Bromoacetate → Methyl 4-(4-cyanophenyl)-1-piperazineacetate

HRID 1757004Notes

Reaction equation

HRID 1757004 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].[H-].[Na+].Br[CH2:18][C:19]([O-:21])=[O:20].[CH3:22]N(C)C=O>O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][N:12]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH2:11][CH2:10]2)=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 6226BromoacetateHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 27339954-(Piperazin-1-yl)benzonitrile

Product 1

HCID 19391362Methyl 4-(4-cyanophenyl)-1-piperazineacetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2 g of 1-(4-cyanophenyl)-piperazine are stirred in 20 ml of dry dimethylformamide at ambient temperature with 0.51 g of a 50% sodium hydride/oil suspension. Whilst cooling in a water bath, 1 ml of bromoacetate is added. Then the mixture is diluted with water and extracted with ethyl acetate. The combined ethyl acetate extracts are dried and the solvent is removed under reduced pressure. The residue remaining is chromatographed with methylene chloride/methanol (98:2) over silica gel. The product is triturated with ether, suction filtered and washed with petroleum ether. Yield: 1.6 g (58% of theory), Melting point: 92°-96° C.

Workup

  1. temperatureWhilst cooling in a water bath
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined ethyl acetate extracts are dried
  4. customthe solvent is removed under reduced pressure
  5. customThe residue remaining is chromatographed with methylene chloride/methanol (98:2) over silica gel
  6. customThe product is triturated with ether, suction
  7. filtrationfiltered
  8. washwashed with petroleum ether

Sources & evidence

ORD record
ord-be70ac56f8c249ba97ef284b4b1414fc
Source dataset
uspto-grants-1995_08
Patent number
US05442064

Reaction notes

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