Carbon Dioxide → 4-(4-Methylpiperazin-1-yl)but-2-ynoic acid

HRID 276823Notes

Reaction equation

HRID 276823 reaction equation
C([Li])CCC.[CH3:6][N:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]#[CH:15])[CH2:9][CH2:8]1.[C:16](=[O:18])=[O:17].O>CCCCCC.O1CCCC1.CO>[CH3:6][N:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]#[C:15][C:16]([OH:18])=[O:17])[CH2:9][CH2:8]1

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 135140911-Methyl-4-(prop-2-yn-1-yl)piperazineHCID 178418339Butyllithium

Product 1

HCID 185489814-(4-Methylpiperazin-1-yl)but-2-ynoic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyl lithium in hexane (17.2 mL, 2.5 M in n-hexane) was slowly added to 1-methyl-4-prop-2-ynyl-piperazine (6.0 g, 43.5 mmol) in 40 mL of tetrahydrofuran under nitrogen. The mixture was stirred for 1 hr at −78° C., then dry carbon dioxide was passed through the reaction overnight. The resulting solution was poured into water and washed with ethyl acetate. The aqueous layer was evaporated under reduced pressure to give the crude acid. The dry acid was dissolved in methanol, and the insoluble salt was removed via filtration. The filtrate was collected and dried in vacuo to give 7 g of 4-(4-methyl-piperazin-1-yl)-but-2-ynoic acid: mass spectrum (m/e):M−H 181.

Workup

  1. washwashed with ethyl acetate
  2. customThe aqueous layer was evaporated under reduced pressure
  3. customto give the crude acid
  4. customthe insoluble salt was removed via filtration
  5. customThe filtrate was collected
  6. customdried in vacuo

Sources & evidence

ORD record
ord-fc0484d8b65f495ea6a58b2b8303d250
Source dataset
uspto-grants-2002_03
Patent number
US06355636B1

Reaction notes

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