N-(2-Aminoethyl)piperidine → N-[2-(1-Piperidinyl)ethyl]-8,9-dihydro-7H-indeno[5,4-e][1,2,4]triazin-3-amine 1-Oxide

HRID 1669004Notes

Reaction equation

HRID 1669004 reaction equation
[N:1]1([CH2:7][CH2:8][NH2:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:11]1[N:12]=[N+:13]([O-:24])[C:14]2[C:23]3[CH2:22][CH2:21][CH2:20][C:19]=3[CH:18]=[CH:17][C:15]=2[N:16]=1>COCCOC>[N:1]1([CH2:7][CH2:8][NH:9][C:11]2[N:12]=[N+:13]([O-:24])[C:14]3[C:23]4[CH2:22][CH2:21][CH2:20][C:19]=4[CH:18]=[CH:17][C:15]=3[N:16]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 33944N-(2-Aminoethyl)piperidineHCID 119505673-Chloro-8,9-dihydro-7H-indeno[5,4-e][1,2,4]triazine 1-Oxide

Product 1

HCID 11950570N-[2-(1-Piperidinyl)ethyl]-8,9-dihydro-7H-indeno[5,4-e][1,2,4]triazin-3-amine 1-OxideYield 93.4%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

2-(1-Piperidinyl)ethylamine (0.32 mL, 2.2 mmol) was added to a stirred solution of chloride 5 (165 mg, 0.7 mmol) in DME (30 mL) and the solution stirred at reflux temperature for 5 h. The solvent was evaporated and the residue was 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 12 (205 mg, 88%) as a pale yellow solid: mp (MeOH) 152-155° C.; 1H NMR δ 7.53 (d, J=8.4 Hz, 1H, H-5), 7.38 (d, J=8.4 Hz, 1H, H-6), 5.90 (br s, 1H, NH), 3.60-3.66 (m, 2H, H-9), 3.48-3.54 (m, 2H, CH2N), 2.97 (br t, J=7.7 Hz, 2H, H-7), 2.57 (dd, J=6.1, 5.9 Hz, 2H, CH2N), 2.38-2.45 (m, 4H, 2×CH2N), 2.17 (br p, J=7.7 Hz, 2H, H-8), 1.55-1.61 (m, 4H, 2×CH2), 1.41-1.48 (m, 2H, CH2); 13C NMR δ 158.4, 149.0, 142.0, 137.3, 132.2, 129.1, 124.6, 56.9, 54.2 (2), 37.9, 35.3, 32.8, 25.9 (2), 24.8, 24.4. Anal. calcd for C17H23N5O: C, 65.2; H, 7.4; N, 22.4. Found: C, 65.1; H, 7.2; N, 22.5%.

Workup

  1. temperatureat reflux temperature for 5 h
  2. customThe solvent was evaporated
  3. customthe residue was 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-77e7b7e1eb354221aa4d8bf9990b27eb
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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