Water → HCID 19884010, compound

HRID 846850Notes

Reaction equation

HRID 846850 reaction equation
O.C(=O)(O)[O-].[Na+].[N:7]1([CH:13]=[O:14])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.[Br:15][CH2:16][CH2:17][C:18](Cl)=[O:19]>C(Cl)Cl>[Br:15][CH2:16][CH2:17][C:18]([N:10]1[CH2:11][CH2:12][N:7]([CH:13]=[O:14])[CH2:8][CH2:9]1)=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 821911-PiperazinecarboxaldehydeHCID 84944Propanoyl chloride, 3-bromo-HCID 516892Sodium Bicarbonate

Product 1

HCID 19884010HCID 19884010, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

A mixture of 15 ml of water and 25 ml of methylene chloride containing 3.0 g (36 mmole) of sodium bicarbonate and 2.82 g (24.7 mmole) of 1-piperazinecarboxaldehyde is stirred and treated with 5.0 g (30.9 mmole) of 3-bromopropionyl chloride in 10 ml of methylene chloride over a 15 minute period while maintaining a temperature of about 20° C. After stirring for an additional 20 minutes, the organic phase is separated and the aqueous phase is extracted with methylene chloride. The combined organic phases are dried (Na2SO4), filtered and concentrated under high vacuum to yield 4.35 g (70.2%) of product as a colorless solid: mp 96°-98° C.

Workup

  1. stirringAfter stirring for an additional 20 minutes
  2. customthe organic phase is separated
  3. extractionthe aqueous phase is extracted with methylene chloride
  4. dry with materialThe combined organic phases are dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under high vacuum

Sources & evidence

ORD record
ord-5731e1b10bcb4890a1cba2d45b90af8d
Source dataset
uspto-grants-1992_08
Patent number
US05138062

Reaction notes

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