1-Methylpiperazine → HCID 178428247, compound

HRID 2386294Notes

Reaction equation

HRID 2386294 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH:8][C:9]2[NH:10][N:11]=[C:12]([CH3:14])[CH:13]=2)[N:5]=[C:4]([S:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([CH:25]3[CH2:27][CH2:26]3)=[O:24])=[CH:18][CH:17]=2)[N:3]=1.[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>>[CH3:28][N:29]1[CH2:34][CH2:33][N:32]([C:2]2[CH:7]=[C:6]([NH:8][C:9]3[NH:10][N:11]=[C:12]([CH3:14])[CH:13]=3)[N:5]=[C:4]([S:15][C:16]3[CH:21]=[CH:20][C:19]([NH:22][C:23]([CH:25]4[CH2:27][CH2:26]4)=[O:24])=[CH:18][CH:17]=3)[N:3]=2)[CH2:31][CH2:30]1

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 178428223HCID 178428223, compound

Product 1

HCID 178428247HCID 178428247, compound

Procedure

Compound D (2.373 g, 5.92 mmol) was treated with N-methylpiperazine (10 ml) and the mixture stirred at 110° for 2 hours. The excess N-methylpiperazine was removed in vacuo then the residue was dissolved in ethyl acetate, washed with aqueous sodium bicarbonate solution, dried over magnesium sulphate, and concentrated. The residue was crystallised from methanol to give colourless crystals of desired product V-1 (1.82 g, 66%), 1H-NMR DMSO-d6, δ 0.81 (4H, d), 1.79 (1H, m), 2.01 (3H, s), 2.18 (3H, s), 2.30 (4H, m), 3.35 (masked signal), 5.42 (1H, s), 6.02 (1H, br s), 7.47 (2H, d), 7.69 (2H, d), 9.22 (1H, s), 10.39 (1H, s), 11.69 (1H, s).

Workup

  1. customThe excess N-methylpiperazine was removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with aqueous sodium bicarbonate solution
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated
  6. customThe residue was crystallised from methanol

Sources & evidence

ORD record
ord-d69d024b65fe43749603834a6c5d3ee0
Source dataset
uspto-grants-2012_09
Patent number
US08268829B2

Reaction notes

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