1-Methylpiperazine → 2-(4-methylpiperazin-1-yl)-N-(prop-2-yn-1-yl)acetamide

HRID 708327Notes

Reaction equation

HRID 708327 reaction equation
Br[CH2:2][C:3]([NH:5][CH2:6][C:7]#[CH:8])=[O:4].[CH3:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1>C(Cl)Cl>[CH3:9][N:10]1[CH2:15][CH2:14][N:13]([CH2:2][C:3]([NH:5][CH2:6][C:7]#[CH:8])=[O:4])[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 111596172-bromo-N-(prop-2-yn-1-yl)acetamide

Product 1

HCID 789125082-(4-methylpiperazin-1-yl)-N-(prop-2-yn-1-yl)acetamideYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-bromo-N-(prop-2-yn-1-yl)acetamide (0.7 g, 3.98 mmol) in DCM (10 mL) added N-methyl piperazine (0.66 mL, 5.96 mmol) drop wise. Reaction mixture stirred at rt for 16 h, diluted with DCM and washed with water and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude residue was triturated with ether-pentane, affording the title compound (0.38 g, 49%); LCMS: m/z=196.15 (M+1); 1H NMR (300 MHz, DMSO-d6) δ 8.06 (d, J=6.1 Hz, 1H), 3.86 (dd, J=5.9, 2.5 Hz, 2H), 3.07 (t, J=2.5 Hz, 1H), 2.91 (s, 2H), 2.47-2.25 (m, 8H), 2.15 (s, 3H).

Workup

  1. customReaction mixture
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was triturated with ether-pentane

Sources & evidence

ORD record
ord-885730bb68a144cb991ec2be0bb66ebd
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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