N-(2-Aminoethyl)piperidine → HCID 11951111, compound

HRID 1669023Notes

Reaction equation

HRID 1669023 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[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][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 33944N-(2-Aminoethyl)piperidineHCID 160813203-Chloro-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazine 1-Oxide

Product 1

HCID 11951111HCID 11951111, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

2-(1-Piperidinyl)ethylamine (0.67 mL, 4.7 mmol) was added to a stirred solution of chloride 21 (348 mg, 1.6 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 36 (465 mg, 95%) as a yellow solid: mp (MeOH/EtOAc) 151-153° C.; 1H NMR δ 8.06 (s, 1H, H-9), 7.39 (s, 1H, H-5), 5.91 (br s, 1H, NH), 3.52-3.57 (m, 2H, CH2N), 2.97-3.03 (m, 4H, H-6, H-8), 2.58 (t, J=6.0 Hz, 2H, CH2N), 2.40-2.47 (m, 4H, 2×CH2N), 2.10-2.18 (m, 2H, H-7), 1.55-1.63 (m, 4H, 2×CH2), 1.42-1.48 (m, 2H, CH2); 13C NMR δ 158.7, 154.5, 148.8, 143.1, 129.7, 120.5, 114.6, 57.0, 54.3 (2), 37.9, 33.1, 32.3, 25.9 (2), 25.7, 24.4. Anal. calcd for C17H23N5O.¼H2O: C, 64.2; H, 7.5; N, 22.0. Found: C, 64.6; H, 6.9; N, 22.1%.

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-a8e5502470c549309aa0d2934e1fee4c
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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