Methylamine → N-methyl-4-(pent-4-ynyl)piperazine-1-carboxamide

HRID 417866Notes

Reaction equation

HRID 417866 reaction equation
[CH2:1]([N:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14]C2C=CC([N+]([O-])=O)=CC=2)=O)[CH2:8][CH2:7]1)[CH2:2][CH2:3][C:4]#[CH:5].[CH3:24][NH2:25]>C1COCC1>[CH3:24][NH:25][C:12]([N:9]1[CH2:8][CH2:7][N:6]([CH2:1][CH2:2][CH2:3][C:4]#[CH:5])[CH2:11][CH2:10]1)=[O:14]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 866082224-Nitrophenyl 4-(pent-4-ynyl)piperazine-1-carboxylate

Product 1

HCID 86608223N-methyl-4-(pent-4-ynyl)piperazine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-nitrophenyl 4-(pent-4-ynyl)piperazine-1-carboxylate (1.37 g) in THF (10 mL) was treated with 40% aq. MeNH2 (10 mL) at 70 C for 2 h. The mixture was concentrated and diluted with conc. NH4OH (5 mL) and water (15 mL). Extraction (DCM, 80 mL) and concentration gave N-methyl-4-(pent-4-ynyl)piperazine-1-carboxamide (0.659 g).

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with conc. NH4OH (5 mL) and water (15 mL)
  3. extractionExtraction (DCM, 80 mL) and concentration

Sources & evidence

ORD record
ord-0edfe2919b6240f0adf1ea6e6ad2e6ce
Source dataset
uspto-grants-2012_01
Patent number
US08093229B2

Reaction notes

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