Propylene Oxide → 3-(2-(4-(2-Hydroxypropyl)piperazin-1-yl)-2-oxoethoxy)benzaldehyde

HRID 592077Notes

Reaction equation

HRID 592077 reaction equation
[O:1]=[C:2]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=[O:9].[CH2:19]1[O:22][CH:20]1[CH3:21]>CO>[OH:22][CH:20]([CH3:21])[CH2:19][N:16]1[CH2:17][CH2:18][N:13]([C:2](=[O:1])[CH2:3][O:4][C:5]2[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=2)[CH:8]=[O:9])[CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 6378Propylene OxideHCID 897262023-(2-Oxo-2-(piperazin-1-yl)ethoxy)benzaldehyde

Product 1

HCID 897258703-(2-(4-(2-Hydroxypropyl)piperazin-1-yl)-2-oxoethoxy)benzaldehydeYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

3-(2-oxo-2-(piperazin-1-yl)ethoxy)benzaldehyde (50) (1 eq) was taken in MeOH to which propylene oxide (4 eq) was added and the reaction mixture was heated in a sealed tube at 70° C. for 16 h when LCMS showed completion of reaction. The reaction mixture was concentrated and purified by column chromatography using silica gel (100-200 mesh) to afford the pure product (50%) as a colorless oil. LCMS: 96.31% (M++1).

Workup

  1. additionwas added
  2. customcompletion of reaction
  3. concentrationThe reaction mixture was concentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-ac2aaff236294d37a7f9809d5ac554c0
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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