(2-Aminoethyl)dipropylamine → N1-(1-Oxido-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazin-3-yl)-N2,N2-dipropyl-1,2-ethanediamine

HRID 1669016Notes

Reaction equation

HRID 1669016 reaction equation
[CH2:1]([N:4]([CH2:8][CH2:9][CH3:10])[CH2:5][CH2:6][NH2:7])[CH2:2][CH3:3].Cl[C:12]1[N:13]=[N+:14]([O-:25])[C:15]2[CH:24]=[C:23]3[C:19]([CH2:20][CH2:21][CH2:22]3)=[CH:18][C:16]=2[N:17]=1>COCCOC>[O-:25][N+:14]1[C:15]2[CH:24]=[C:23]3[C:19](=[CH:18][C:16]=2[N:17]=[C:12]([NH:7][CH2:6][CH2:5][N:4]([CH2:8][CH2:9][CH3:10])[CH2:1][CH2:2][CH3:3])[N:13]=1)[CH2:20][CH2:21][CH2:22]3

Participants

4

Reactant 2

HCID 5151220(2-Aminoethyl)dipropylamineHCID 160813203-Chloro-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazine 1-Oxide

Product 1

HCID 11950938N1-(1-Oxido-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazin-3-yl)-N2,N2-dipropyl-1,2-ethanediamineYield 75.9%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

N1,N1-Dipropyl-1,2-ethanediamine (297) (0.27 g, 1.9 mmol) was added to a stirred solution of chloride 21 (298 mg, 1.3 mmol) in DME (50 mL) and the solution stirred at reflux temperature for 2 h. The solvent was evaporated and the residue partitioned between DCM (100 mL) and dilute aqueous NH3 solution (50 mL). The organic fraction was dried and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (0-10%) of MeOH/DCM, to give 1-oxide 28 (325 mg, 74%) as a yellow powder: mp (MeOH/EtOAc) 95-97° C.; 1H NMR δ 8.07 (s, 1H, H-9), 7.39 (s, 1H, H-5), 5.80 (br s, 1H, NH), 3.46-3.53 (m, 2H, CH2N), 2.96-3.03 (m, 4H, 2×CH2N), 2.68 (dd, J=6.0, 5.8 Hz, 2H, CH2N), 2.38-2.45 (m, 4H, H-6, H-8), 2.10-2.18 (m, 2H, H-7), 1.41-1.51 (m, 4H, 2×CH2), 0.87 (t, J=7.1 Hz, 6H, 2×CH3); 13C NMR δ 158.7, 154.4, 148.8, 143.0, 129.8, 120.5, 114.7, 55.9 (2), 52.6, 38.9, 31.1, 32.3, 25.7, 20.3 (2), 11.9 (2). Anal. calcd for C18H27N5O: C, 65.6; H, 8.3; N, 21.3. Found: C, 65.4; H, 8.4; N, 21.3%.

Workup

  1. temperatureat reflux temperature for 2 h
  2. customThe solvent was evaporated
  3. customthe residue partitioned between DCM (100 mL) and dilute aqueous NH3 solution (50 mL)
  4. customThe organic fraction was dried
  5. customthe solvent evaporated
  6. customThe residue was purified by chromatography
  7. washeluting with a gradient (0-10%) of MeOH/DCM

Sources & evidence

ORD record
ord-ae2bed47e6b041a684cf5b596e2c33bd
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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