1-Methylpiperazine → HCID 67382819, compound

HRID 2176925Notes

Reaction equation

HRID 2176925 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH2:8][C:9]([O:11]C(C)(C)C)=O)[CH:5]=[CH:4][N:3]=1.[CH3:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>O>[CH3:16][N:17]1[CH2:22][CH2:21][N:20]([C:9](=[O:11])[CH2:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([N:20]3[CH2:21][CH2:22][N:17]([CH3:16])[CH2:18][CH2:19]3)[CH:7]=2)[CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 86623474HCID 86623474, compound

Product 1

HCID 67382819HCID 67382819, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A suspension of tert-butyl 2-(2-chloropyridin-4-yl)acetate (600 mg, 2.64 mmol) and N-methyl piperazine (2 ml) was heated in a sealed tube for 24 h at 140° C. The reaction mixture was cooled to room temperature, water was added and extracted with DCM. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to get the crude product. Purification by column chromatography over neutral alumina using 5% MeOH in CHCl3 as eluent afforded 600 mg (71%) of 1-(4-methylpiperazin-1-yl)-2-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)ethanone as colorless liquid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with DCM
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customto get the crude product
  8. customPurification by column chromatography over neutral alumina using 5% MeOH in CHCl3 as eluent

Sources & evidence

ORD record
ord-faa73ecd9e5a4849a3762341043ae6b9
Source dataset
uspto-grants-2015_06
Patent number
US09067888B2

Reaction notes

Loading…