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

HRID 548455Notes

Reaction equation

HRID 548455 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, 2.5M 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 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-a0f31fd0f14d4f62a20fdf7b28db26cd
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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