1-Methylpiperazine → HCID 69226317, compound

HRID 1027880Notes

Reaction equation

HRID 1027880 reaction equation
CS([C:5]1[C:18]2[O:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[N:8]=[C:7]([NH2:19])[N:6]=1)(=O)=O.[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>COCCO>[CH3:20][N:21]1[CH2:26][CH2:25][N:24]([C:5]2[C:18]3[O:17][CH2:16][C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:9]=3[N:8]=[C:7]([NH2:19])[N:6]=2)[CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 69099358HCID 69099358, compound

Product 1

HCID 69226317HCID 69226317, compound

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of Example 41C, 1-methyl-piperazine (0.5 mL) and 2-methoxy-ethanol (1 mL) was heated at 110° C. for 60 hours, cooled, concentrated under reduced pressure and chromatographed on silica gel eluting with a gradient of 2, 3.5 and 5% (9:1 MeOH: saturated aqueous NH4OH) to provide the title compound. 1H NMR (CDCl3) δ 2.34 (s, 3H), 2.52 (t, J=4.75 Hz, 4H), 3.83 (t, J=4.75 Hz, 4H), 4.61 (s, 2H), 5.06 (s, 2H), 7.12 (m, 1H), 7.34-7.44 (m, 2H), 8.05 (m, 1H); MS (M+H)+ m/z 298.

Workup

  1. temperaturecooled
  2. concentrationconcentrated under reduced pressure
  3. customchromatographed on silica gel eluting with a gradient of 2, 3.5 and 5% (9:1 MeOH: saturated aqueous NH4OH)

Sources & evidence

ORD record
ord-0dc60059c8684e05b4a3cae387c19208
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

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