Ethyl bromoacetate → HCID 12899521, compound

HRID 569969Notes

Reaction equation

HRID 569969 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:12]=2[CH2:13][CH2:14][C:15](=[O:21])[NH:16]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CN(C)C=O>[C:24]([O:26][CH2:27][CH2:28][N:4]1[CH2:5][CH2:6][N:1]([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:12]=2[CH2:13][CH2:14][C:15](=[O:21])[NH:16]3)[CH2:2][CH2:3]1)(=[O:25])[CH3:23]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 14128502HCID 14128502, compound

Product 1

HCID 12899521HCID 12899521, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

20 Grams of 5-(3-piperazinylpropoxy)-3,4-dihydrocarbostyril and 3 ml of ethyl 2-bromoacetate and 1.5 ml of triethylamine are mixed with 20 ml of dimethyl formamide at 50°-60° C. for 8 hours under stirring conditions. The reaction mixture is concentrated under reduced pressure and to the viscous residue thus obtained are added 30 ml of 2% sodium hydrogencarbonate aqueous solution followed by extraction with chloroform. The chloroform layer is washed with water, dried and chloroform is removed by distillation. The residue is purified by silica gel chromatography and recrystallized from isopropanol to obtain 5-{3-[4-(2-acetyloxyethyl)piperazinyl]propoxy}-3,4-dihydrocarbostyril in the form of colorless needle-like crystals with a melting point of 131°-132° C.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure and to the viscous residue
  2. customthus obtained
  3. extractionfollowed by extraction with chloroform
  4. washThe chloroform layer is washed with water
  5. customdried
  6. customchloroform is removed by distillation
  7. customThe residue is purified by silica gel chromatography
  8. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-04326ee31ad5401498f619d3202258ed
Source dataset
uspto-grants-1988_03
Patent number
US04734416

Reaction notes

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