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

HRID 1669025Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1669025
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH3:8])[N:3]1[CH2:9][CH2:10][NH2:11].Cl[C:13]1[N:14]=[N+:15]([O-:26])[C:16]2[CH:25]=[C:24]3[C:20]([CH2:21][CH2:22][CH2:23]3)=[CH:19][C:17]=2[N:18]=1>COCCOC>[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH3:8])[N:3]1[CH2:9][CH2:10][NH:11][C:13]1[N:14]=[N+:15]([O-:26])[C:16]2[CH:25]=[C:24]3[C:20]([CH2:21][CH2:22][CH2:23]3)=[CH:19][C:17]=2[N:18]=1

Komponenten

4

Edukt 2

HCID 31492662,6-Dimethyl-1-piperidineethanamineHCID 160813203-Chloro-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazine 1-Oxide

Produkt 1

HCID 11951113N-[2-(2,6-Dimethyl-1-piperidinyl)ethyl]-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazin-3-amine 1-OxideAusbeute 81,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

2-(2,6-Dimethyl-1-piperidinyl)ethylamine (280) (0.66 g, 4.3 mmol) was added to a stirred solution of chloride 21 (314 mg, 1.4 mmol) in DME (50 mL) and the solution stirred at reflux temperature for 3 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 38 (389 mg, 80%) as a yellow solid: mp (MeOH) 173-175° C.; 1H NMR δ 8.07 (s, 1H, H-9), 7.38 (s, 1H, H-5), 5.47 (br s, 1H, NH), 3.50-3.55 (m, 2H, CH2N), 2.96-3.03 (m, 4H, CH2N, CH2), 2.87-2.91 (m, 2H, CH2), 2.48-2.57 (m, 2H, CH2N), 2.10-2.18 (m, 2H, CH2), 1.64-1.69 (m, 1H, CH2), 1.53-1.58 (m, 2H, CH2), 1.33-1.38 (m, 1H, CH2), 1.24-1.31 (m, 2H, CH2), 1.20 (d, J=6.3 Hz, 6H, 2×CH3); 13C NMR δ 158.8, 154.5, 148.8, 143.2, 129.8, 120.6, 114.7, 57.2 (2), 47.5, 39.4, 34.3, 33.1 (2), 32.3, 25.8, 24.4, 21.7 (2). Anal. calcd for C19H27N5O: C, 66.8; H, 8.0; N, 20.5. Found: C, 66.8; H, 7.8; N, 20.6%.

Aufarbeitung

  1. temperatureat reflux temperature for 3 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

Quellen und Nachweise

ORD-Eintrag
ord-7ca3517007654e99aa0196d9b8d06ae2
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989451B2

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