1-Methylpiperazine → (4-Methylpiperazin-1-yl){4-[(trimethylsilyl)ethynyl]phenyl}methanone

HRID 1403193Notes

Reaction equation

HRID 1403193 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[CH3:30][Si:31]([C:34]#[C:35][C:36]1[CH:44]=[CH:43][C:39]([C:40](O)=[O:41])=[CH:38][CH:37]=1)([CH3:33])[CH3:32]>C(Cl)Cl>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:40]([C:39]2[CH:43]=[CH:44][C:36]([C:35]#[C:34][Si:31]([CH3:30])([CH3:33])[CH3:32])=[CH:37][CH:38]=2)=[O:41])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 136281904-[(Trimethylsilyl)ethynyl]benzoic acid

Product 1

HCID 71239568(4-Methylpiperazin-1-yl){4-[(trimethylsilyl)ethynyl]phenyl}methanoneYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Methylpiperazine (0.66 mL, 6.0 mmol), HOBt (0.84 g, 6.2 mmol) and EDCl (1.15 g, 6.0 mmol) were added to a solution of 4-[(trimethylsilyl)ethynyl]benzoic acid (1.0 g, 4.6 mmol) in dry DCM (45 mL). The mixture was stirred at room temperature for 4 h, washed with saturated aqueous sodium bicarbonate (30 mL), brine, dried over sodium sulphate, and evaporated. The crude was purified by flash chromatography on silica gel (DCM/MeOH 96/4) to afford the title compound (1.29 g, 93%).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate (30 mL), brine
  2. dry with materialdried over sodium sulphate
  3. customevaporated
  4. customThe crude was purified by flash chromatography on silica gel (DCM/MeOH 96/4)

Sources & evidence

ORD record
ord-dee5acb81e2e4641a78d4ca58c28f42c
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

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