2-Morpholinoethylamine → N-[2-(4-Morpholinyl)ethyl]-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazin-3-amine 1-Oxide

HRID 1669032Notes

Reaction equation

HRID 1669032 reaction equation
[N:1]1([CH2:7][CH2:8][NH2:9])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[C:11]1[N:12]=[N+:13]([O-:24])[C:14]2[CH:23]=[C:22]3[C:18]([CH2:19][CH2:20][CH2:21]3)=[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[CH:23]=[C:22]4[C:18]([CH2:19][CH2:20][CH2:21]4)=[CH:17][C:15]=3[N:16]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 160813203-Chloro-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazine 1-Oxide

Product 1

HCID 11951284N-[2-(4-Morpholinyl)ethyl]-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazin-3-amine 1-OxideYield 98%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

2-(4-Morpholinyl)ethylamine (3.93 mL, 30.0 mmol) was added to a stirred solution of chloride 21 (2.21 g, 10.0 mmol) in DME (50 mL) and the solution stirred at reflux temperature for 3 h. The solvent was evaporated and the residue stirred with water (150 mL) at room temperature for 30 min. The solid was filtered, washed with water (3×10 mL) and dried to give 1-oxide 44 (3.08 g, 98%) as an orange solid: mp (water) 178-179° C.; 1H NMR δ 8.07 (s, 1H, H-9), 7.39 (s, 1H, H-5), 5.79 (br s, 1H, NH), 3.72 (br t, J=4.6 Hz, 4H, CH2O), 3.59 (q, J=5.6 Hz, 2H, CH2N), 2.97-3.05 (m, 4H, H-6, H-8), 2.63 (t, J=5.9 Hz, 2H, CH2N), 2.51 (br t, J=4.6 Hz, 4H, CH2N), 2.10-2.19 (m, 2H, H-7); 13C NMR δ 158.6, 154.6, 148.7, 143.3, 129.8, 120.5, 114.6, 66.9 (2), 56.8, 53.3 (2), 37.5, 33.1, 32.3, 25.7. Anal. calcd for C16H21N5O2: C, 60.9; H, 6.7; N, 22.2. Found: C, 61.0; H, 6.8; N, 22.3%.

Workup

  1. temperatureat reflux temperature for 3 h
  2. customThe solvent was evaporated
  3. stirringthe residue stirred with water (150 mL) at room temperature for 30 min
  4. filtrationThe solid was filtered
  5. washwashed with water (3×10 mL)
  6. customdried

Sources & evidence

ORD record
ord-2cf4744bf1b44bc78b60ea6c16a6358d
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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