Methylamine → 4-(but-3-ynyl)-N-methylpiperazine-1-carboxamide

HRID 1984104Notes

Reaction equation

HRID 1984104 reaction equation
[CH2:1]([N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)[CH2:2][C:3]#[CH:4].[C:11](Cl)(=[O:22])OC1C=CC([N+]([O-])=O)=CC=1.C[CH2:25][N:26](CC)CC.CN>C1COCC1.CO.O>[CH2:1]([N:5]1[CH2:10][CH2:9][N:8]([C:11]([NH:26][CH3:25])=[O:22])[CH2:7][CH2:6]1)[CH2:2][C:3]#[CH:4]

Participants

8

Reactant 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 247002581-(But-3-yn-1-yl)piperazine

Product 1

HCID 866082284-(but-3-ynyl)-N-methylpiperazine-1-carboxamide

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(but-3-ynyl)piperazine (445 mg) in THF (4 mL) was treated with 4-nitrophenyl carbonochloridate (649 mg) at rt for 5 min. A precipitate formed immediately, and the suspension was treated with Et3N (0.45 mL) to ensure complete reaction. The suspension was diluted wiht H2O (2 mL), MeOH (2 mL) and 40% aq. MeNH2 (4.0 mL) and stirred at rt for 3 days. Extraction with DCM (50 mL), washing (NaOH 2M), drying (Na2SO4) and concentration gave 4-(but-3-ynyl)-N-methylpiperazine-1-carboxamide (370 mg).

Workup

  1. customA precipitate formed immediately
  2. customreaction
  3. extractionExtraction with DCM (50 mL)
  4. washwashing (NaOH 2M)
  5. customdrying
  6. concentration(Na2SO4) and concentration

Sources & evidence

ORD record
ord-ac0dbd410b8f4fc09a0ed6f16b0e2ae8
Source dataset
uspto-grants-2009_06
Patent number
US07544672B2

Reaction notes

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